Ligands Derived from Carbohydrates for Asymmetric Catalysis

Chemical Reviews - Tập 104 Số 6 - Trang 3189-3216 - 2004
Montserrat Diéguez1, Òscar Pàmies1, Carmen Claver1
1Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Pl. Imperial Tàrraco 1, 43005 Tarragona, Spain

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Tài liệu tham khảo

See, 1994, R. Asymmetric Catalysis in Organic Synthesis

Blaser H.-U., 1992, Chem. Rev., 92, 935, 10.1021/cr00013a009

RajanBabu T. V., 1994, Pure Appl. Chem., 66, 1535, 10.1351/pac199466071535

Ayers T. A., 1999, Process Chemistry in the Pharmaceutical Industry, 345

Chen M., 2000, Fenzi Cuihua, 14, 441

Liu X., 2001, Youji Huaxue, 21, 191

Ohe K., 2001, Yuki Gosei Kagaku Kyokaishi, 59, 185, 10.5059/yukigoseikyokaishi.59.185

RajanBabu T. V., 2003, Chem. Rev., 103, 2645, 10.1021/cr020040g

For, 2000, Coord. Chem. Rev., 203, 81, 10.1016/S0010-8545(99)00183-6

Kagan H. N., 1972, J. Am. Chem. Soc., 94, 6430, 10.1021/ja00773a028

Nagel U., 1986, Chem. Ber., 119, 3326, 10.1002/cber.19861191112

Nagel U., 1989, Organometallics, 8, 1534, 10.1021/om00108a026

Lafont D., 1979, J. Organomet. Chem., 169, 87, 10.1016/S0022-328X(00)81459-X

Bakos J., 1983, J. Organomet. Chem., 253, 249, 10.1016/0022-328X(83)80123-5

Johnson T. H., 1980, J. Org. Chem., 45, 62, 10.1021/jo01289a013

Habuűs I., 1988, Croat. Chim. Acta, 61, 857

S̋unjić V., 1989, Gazz. Chim. Ital., 119, 229

Li C., 1991, Carbohydr. Res., 149

Choudary B. M., 1994, Indian J. Chem. B, 33, 152

Gilbertson S. R., 1995, J. Org. Chem., 60, 6226, 10.1021/jo00124a051

Brunner H., 1987, J. Organomet. Chem., 328, 71, 10.1016/S0022-328X(00)99768-7

Brunner H., 1980, J. Chem. Res. (S), 76

Yamashita M., 1982, Bull. Chem. Soc. Jpn., 55, 2917, 10.1246/bcsj.55.2917

Saito S., 1985, Chem. Pharm. Bull., 33, 5284, 10.1248/cpb.33.5284

Iida A., 1988, Bull. Chem. Soc. Jpn., 61, 2365, 10.1246/bcsj.61.2365

Lemaux P., 1985, J. Organomet. Chem., 284, 101, 10.1016/0022-328X(85)80015-2

Cullen W. R., 1978, Tetrahedron Lett., 1635, 10.1016/S0040-4039(01)94626-X

Jackson R., 1978, J. Organomet. Chem., 159, C29, 10.1016/S0022-328X(00)92235-6

Selke R., 1979, React. Kinet. Catal. Lett., 10, 135, 10.1007/BF02075980

Selke R., 1986, J. Mol. Catal., 37, 213, 10.1016/0304-5102(86)85010-6

Selke R., 1987, J. Prakt. Chem., 329, 717, 10.1002/prac.19873290422

Selke R., 1989, J. Organomet. Chem., 370, 249, 10.1016/0022-328X(89)87288-2

Selke R., 1993, J. Mol. Catal., 84, 223, 10.1016/0304-5102(93)85056-Y

Sinou D., 1980, React. Kinet. Catal. Lett., 14, 463, 10.1007/BF02061353

RajanBabu T. V., 1992, J. Am. Chem. Soc., 114, 6265, 10.1021/ja00041a066

Casalnuovo A. L., 1994, J. Am. Chem. Soc., 116, 9869, 10.1021/ja00101a007

Habuš I., 1987, J. Mol. Catal., 42, 173, 10.1016/0304-5102(87)85023-X

Snatze G., 1988, Carbohydr. Res., 182, 179, 10.1016/0008-6215(88)84002-3

Yamashita M., 1989, Bull. Chem. Soc. Jpn., 62, 942, 10.1246/bcsj.62.942

Yamashita M., 1986, Bull. Chem. Soc. Jpn., 59, 175, 10.1246/bcsj.59.175

Bendayan A., 1993, J. Organomet. Chem., 444, 41, 10.1016/0022-328X(93)83052-W

Seebach D., 1995, Helv. Chim. Acta, 78, 1636, 10.1002/hlca.19950780703

Wink D. J., 1990, Inorg. Chem., 29, 5006, 10.1021/ic00349a035

Sakaki J., 1993, Helv. Chim. Acta, 76, 2654, 10.1002/hlca.19930760722

Buisman G. J. H., 1993, Tetrahedron: Asymmetry, 4, 1625, 10.1016/S0957-4166(00)80370-5

Buisman G. J., 1995, Tetrahedron: Asymmetry, 8, 719, 10.1016/0957-4166(95)00068-Z

James B. R., 1977, Can. J. Chem., 55, 3927, 10.1139/v77-556

Katsuki T., 1980, J. Am. Chem. Soc., 102, 5974, 10.1021/ja00538a077

Schmidt B., 1991, Angew. Chem., Int. Ed. Engl., 30, 99, 10.1002/anie.199100991

Masaki Y., 1992, Tetrahedron Lett., 33, 5089, 10.1016/S0040-4039(00)61197-8

Spescha M., 1993, Helv. Chim. Acta, 76, 1832, 10.1002/hlca.19930760504

Collman J. P., 1995, J. Am. Chem. Soc., 117, 692, 10.1021/ja00107a013

Peña D., 2002, J. Am. Chem. Soc., 124, 14552, 10.1021/ja028235t

(a) Hu, W.; Chen, C. C.; Xue, G.; Chan, A. S. C.Tetrahedron:  Asymmetry1998,9, 4183.

(b) Robert, F.; Oehme, G.; Sinou, D.J.Mol.Catal.A: Chem.1999,139, 105.

Guillaneux D., 2000, Collect. Czech. Chem. Commun., 65, 717, 10.1135/cccc20000717

Yan Y. Y., 2000, Org. Lett., 2, 4137, 10.1021/ol006591f

Li W., 2000, J. Org. Chem., 65, 5871, 10.1021/jo0004613

Zhang X. U.S., 2001, Patent WO 01/34612 A2

Li W., 2002, J. Org. Chem., 67, 7618, 10.1021/jo020250t

Holz J., 1998, J. Org. Chem., 63, 8031, 10.1021/jo980960s

Holz J., 2001, Eur. J. Org. Chem., 4615, 10.1002/1099-0690(200112)2001:24<4615::AID-EJOC4615>3.0.CO;2-N

Stürner R., 2002, Patent 6359165 B1

Li W., 2000, J. Org. Chem., 65, 3489, 10.1021/jo000066c

Liu D., 2002, Org. Lett., 4, 4471, 10.1021/ol0269998

Zhang X., 2003, Patent WO 03/040149 A2

Bayer A., 2002, Eur. J. Inorg. Chem., 2614, 10.1002/1099-0682(200210)2002:10<2614::AID-EJIC2614>3.0.CO;2-2

Carmichael D., 1999, Chem. Commun., 261, 10.1039/a808711c

Holz J., 1999, Tetrahedron Lett., 40, 7059, 10.1016/S0040-4039(99)01458-6

RajanBabu T. V., 2001, J. Am. Chem. Soc., 123, 10207, 10.1021/ja011500a

Pàmies O., 2000, Eur. J. Inorg. Chem., 2011, 10.1002/1099-0682(200009)2000:9<2011::AID-EJIC2011>3.0.CO;2-#

Diéguez M., 2000, Tetrahedron: Asymmetry, 11, 4701, 10.1016/S0957-4166(00)00440-7

RajanBabu T. V., 1994, J. Am. Chem. Soc., 116, 4101, 10.1021/ja00088a065

RajanBabu T. V., 1997, J. Org. Chem., 62, 6012, 10.1021/jo970884d

Ayers T. A., 1996, Patent 5510507

Yan Y. Y., 2001, J. Org. Chem., 66, 3277, 10.1021/jo001686g

Yonehara K., 1998, Bull. Chem. Soc. Jpn., 71, 1967, 10.1246/bcsj.71.1967

Yonehara K., 1999, J. Org. Chem., 64, 9381, 10.1021/jo9912505

Yonehara K., 1999, J. Org. Chem., 64, 5593, 10.1021/jo990448m

Shin S., 1999, Org. Lett., 1, 1229, 10.1021/ol9908979

Chen Y., 1999, Tetrahedron Lett., 40, 957, 10.1016/S0040-4039(98)02457-5

Faltin F., 2001, Synthesis, 638, 10.1055/s-2001-12357

Guimet E., 2001, Universitat Rovira i Virgili

Kadyrov R., 1999, Tetrahedron: Asymmetry, 9, 329, 10.1016/S0957-4166(97)00622-8

Reetz M. T., 1999, Angew. Chem., Int. Ed., 38, 179, 10.1002/(SICI)1521-3773(19990115)38:1/2<179::AID-ANIE179>3.0.CO;2-Z

Pàmies O., 2000, Eur. J. Inorg. Chem., 1287, 10.1002/(SICI)1099-0682(200006)2000:6<1287::AID-EJIC1287>3.3.CO;2-G

Pàmies O., 2000, Tetrahedron: Asymmetry, 11, 1097, 10.1016/S0957-4166(00)00061-6

Diéguez M., 2002, J. Org. Chem., 67, 3796, 10.1021/jo0255429

Diéguez M., 2003, Dalton Trans., 2957, 10.1039/B303303A

Claver C., 2000, Chem. Commun., 961

Reetz M. T., 2002, Tetrahedron Lett., 43, 7941, 10.1016/S0040-4039(02)01838-5

Reetz M. T., 2000, Angew. Chem., Int. Ed., 39, 3889, 10.1002/1521-3773(20001103)39:21<3889::AID-ANIE3889>3.0.CO;2-T

Reetz M. T., 2003, Org. Lett., 5, 3099, 10.1021/ol035076p

Huang H., 2003, Org. Lett., 5, 4137, 10.1021/ol035551j

van den Berg M., 2003, Adv. Synth. Catal., 345, 308, 10.1002/adsc.200390026

Diéguez M., 1997, J. Chem. Soc., Dalton Trans., 4611, 10.1039/a704611a

Diéguez M., 1998, J. Chem. Soc., Dalton Trans., 3517, 10.1039/a803626h

Pàmies O., 1999, J. Chem. Soc., Dalton Trans., 3439, 10.1039/a905396d

Reetz M. T., 1999, Tetrahedron: Asymmetry, 10, 2129, 10.1016/S0957-4166(99)00215-3

Ohe K., 2002, Tetrahedron: Asymmetry, 13, 2155, 10.1016/S0957-4166(02)00569-4

Robert F., 2000, J. Organomet. Chem., 604, 99, 10.1016/S0022-328X(00)00208-4

Pàmies O., 2000, Organometallics, 19, 1488, 10.1021/om990638n

Pàmies O., 2000, Chem. Commun., 2383, 10.1039/b007850f

Pàmies O., 2001, J. Org. Chem., 66, 8364, 10.1021/jo0157122

Diéguez M., 2001, Chem. Commun., 2702, 10.1039/b109043g

Hildraf R., 1999, Synlett, 1814, 10.1055/s-1999-2939

Tatarov V. I., 1999, Tetrahedron: Asymmetry, 10, 4009, 10.1016/S0957-4166(99)00431-0

Guiu E., 2003, Adv. Synth. Catal., 345, 169, 10.1002/adsc.200390005

Beller M., 1995, J. Mol. Catal., 104, 17, 10.1016/1381-1169(95)00130-1

Agboussou F., 1995, Chem. Rev., 95, 2485, 10.1021/cr00039a008

van Leeuwen P. W. N. M., 2000, Rhodium Catalyzed Hydroformylation

Stille J. K., 1991, Organometallics, 10, 1183, 10.1021/om00050a060

Consiglio G., 1991, Organometallics, 10, 2046, 10.1021/om00052a061

Diéguez, M.; Pereira, M. M.; Masdeu Bultó, A. M.; Claver, C.; Bayón, J. C.JMol.Catal.A:  Chem.1999,143, 111 and references therein.

Nozaki K., 1997, J. Am. Chem. Soc., 119, 4413, 10.1021/ja970049d

Franció G., 1999, Chem. Commun., 1663, 10.1039/a904281d

(c) Babin, J. E.; Whiteker, G. T. WO 93/03839, 1993.

Buisman G. J. H., 1997, Organometallics, 16, 2929, 10.1021/om970172d

Liu S., 2000, Catal. Today, 63, 531, 10.1016/S0920-5861(00)00500-9

Diéguez M., 2001, Tetrahedron: Asymmetry, 12, 651, 10.1016/S0957-4166(01)00081-7

RajanBabu T. V., 1994, Tetrahedron Lett., 35, 4295, 10.1016/S0040-4039(00)73337-5

Ayers T. A., 1995, Patent 5475146

Ayers T. A., 1996, Patent 5574171

Diéguez M., 2000, Chem. Commun., 1607, 10.1039/b004799f

Diéguez M., 2001, Chem. Eur. J., 7, 3086, 10.1002/1521-3765(20010716)7:14<3086::AID-CHEM3086>3.0.CO;2-O

Diéguez M., 2002, New. J. Chem., 26, 827, 10.1039/b200669c

Kless A., 1996, Tetrahedron: Asymmetry, 7, 33, 10.1016/0957-4166(95)00414-9

Chelucci G., 1996, Tetrahedron: Asymmetry, 7, 885, 10.1016/0957-4166(96)00086-9

Aghmiz, A.; Masdeu-Bultó, A. M.; Claver, C.; Sinou, D.J.Mol.Catal.A: Chem.2002,184, 111.

Pàmies O., 2001, Tetrahedron: Asymmetry, 12, 3441, 10.1016/S0957-4166(02)00030-7

Diéguez M., 2001, Tetrahedron: Asymmetry, 12, 2827, 10.1016/S0957-4166(01)00489-X

Orejón A., 1998, J. Organomet. Chem., 559, 23, 10.1016/S0022-328X(97)00692-X

Diéguez M., 1999, Inorg. Chim. Acta, 295, 64, 10.1016/S0020-1693(99)00309-6

Trost B. M., 1996, Chem. Rev., 96, 395, 10.1021/cr9409804

Johannsen M., 1998, Chem. Rev., 98, 1869, 10.1021/cr970343o

For, 1998, Tetrahedron: Asymmetry, 9, 1, 10.1016/S0957-4166(97)00593-4

Masdeu-Bultó A. M., 2003, Coord. Chem. Rev., 242, 159, 10.1016/S0010-8545(03)00106-1

Pàmies O., 2000, Monatsch. Chem., 131, 1173, 10.1007/s007060070025

Diéguez M., 2001, Chem. Commun., 1132, 10.1039/b101567m

Yan Y. Y., 2000, Org. Lett., 2, 199, 10.1021/ol991285r

Zhang X., 2003, WO Patent 03/040149 A2

Nomura N., 1996, Synlett, 745, 10.1055/s-1996-5534

Clyne D. S., 1999, J. Org. Chem., 64, 7601, 10.1021/jo9911387

Pàmies O., 2001, J. Org. Chem., 66, 8867, 10.1021/jo0159284

Jansat S., 2001, Tetrahedron: Asymmetry, 12, 1469, 10.1016/S0957-4166(01)00260-9

Khiar N., 2003, Tetrahedron Lett., 44, 3401, 10.1016/S0040-4039(03)00568-9

Albinati A., 1996, Organometallics, 15, 2419, 10.1021/om950983m

Barbaro P., 1996, Organometallics, 15, 1879, 10.1021/om9509204

Nakano H., 2003, Tetrahedron: Asymmetry, 14, 2361, 10.1016/S0957-4166(03)00495-6

Robert, F.; Gaillard, N.; Sinou, D.J.Mol.Catal.A:  Chem.1999,144, 473.

Borriello C., 2003, Inorg. Chim. Acta, 353, 238, 10.1016/S0020-1693(03)00230-5

Brunner H., 2003, Tetrahedron: Asymmetry, 14, 1115, 10.1016/S0957-4166(03)00093-4

Gläser B., 1998, Synlett, 53, 10.1055/s-1998-3124

Yonehara K., 1999, Chem. Commun., 415, 10.1039/a810041a

Hashizume T., 2000, J. Org. Chem., 65, 5197, 10.1021/jo000305w

Boog-Wick K., 1998, Organometallics, 17, 3254, 10.1021/om9802010

For, 1998, Angew. Chem., Int. Ed., 37, 283, 10.1002/(SICI)1521-3773(19980216)37:3<283::AID-ANIE283>3.0.CO;2-9

Feringa B. L., 2000, Acc. Chem. Res., 33, 346, 10.1021/ar990084k

Hu X., 1999, Angew. Chem., Int. Ed., 38, 3518, 10.1002/(SICI)1521-3773(19991203)38:23<3518::AID-ANIE3518>3.0.CO;2-P

Knöbel A. K. H., 1997, Synlett, 1429

Yan M., 1999, Chem. Commun., 11, 10.1039/a807997h

Yan M., 2000, Chem. Commun., 115, 10.1039/a908467c

Chataigner I., 2000, Angew. Chem., Int. Ed., 39, 916, 10.1002/(SICI)1521-3773(20000303)39:5<916::AID-ANIE916>3.0.CO;2-M

Chataigner I., 2001, Chem. Eur. J., 7, 2628, 10.1002/1521-3765(20010618)7:12<2628::AID-CHEM26280>3.0.CO;2-7

Alexakis A., 2000, Eur. J. Org. Chem., 4011, 10.1002/1099-0690(200012)2000:24<4011::AID-EJOC4011>3.0.CO;2-D

Alexakis A., 2000, Org. Lett., 2, 2579, 10.1021/ol0059596

Alexakis A., 2001, Tetrahedron: Asymmetry, 12, 1151, 10.1016/S0957-4166(01)00196-3

Pàmies O., 1999, Tetrahedron: Asymmetry, 10, 2007, 10.1016/S0957-4166(99)00197-4

Pàmies O., 2000, Tetrahedron: Asymmetry, 11, 4377, 10.1016/S0957-4166(00)00430-4

Diéguez M., 2001, Tetrahedron: Asymmetry, 12, 2895, 10.1016/S0957-4166(01)00514-6

Alexakis A., 1998, Tetrahedron Lett., 39, 7869, 10.1016/S0040-4039(98)01761-4

Mandoli A., 2001, L Tetrahedron: Asymmetry, 12, 1929, 10.1016/S0957-4166(01)00348-2

Kelle E., 1998, Tetrahedron Asymmetry, 9, 2409, 10.1016/S0957-4166(98)00240-7

Duursma A., 2002, Tetrahedron, 58, 5773, 10.1016/S0040-4020(02)00574-4

Pigro M. C., 2002, Tetrahedron, 58, 5459, 10.1016/S0040-4020(02)00510-0

Seebach D., 1997, Helv. Chim. Acta, 80, 2515, 10.1002/hlca.19970800819

Pichota A., 2000, Angew. Chem., Int. Ed., 39, 153, 10.1002/(SICI)1521-3773(20000103)39:1<153::AID-ANIE153>3.0.CO;2-N

Pàmies O., 2000, Tetrahedron: Asymmetry, 11, 871, 10.1016/S0957-4166(99)00546-7

Diéguez M., 2001, Tetrahedron: Asymmetry, 12, 2861, 10.1016/S0957-4166(01)00512-2

Diéguez, M.; Pàmies, O.; Net, G.; Ruiz, A.; Claver, C.J.Mol.Catal.A: Chem.2002,185, 11.

Seebach D., 2001, Angew. Chem., Int. Ed., 40, 92, 10.1002/1521-3773(20010105)40:1<92::AID-ANIE92>3.0.CO;2-K

Cho B. T., 1996, J. Chem. Soc., Perkin Trans. 1, 2901, 10.1039/P19960002901

Bauer T., 2002, Tetrahedron: Asymmetry, 13, 77, 10.1016/S0957-4166(02)00053-8

Huang H., 2003, Tetrahedron: Asymmetry, 14, 297, 10.1016/S0957-4166(02)00861-3

Huang H., 2003, Tetrahedron: Asymmetry, 14, 1285, 10.1016/S0957-4166(03)00212-X

Yonehara K., 2000, J. Organomet. Chem., 603, 40, 10.1016/S0022-328X(00)00069-3

Imbos R., 2002, J. Am. Chem. Soc., 124, 184, 10.1021/ja017200a

Imbos R., 2003, Dalton Trans., 2017, 10.1039/B300565H

Blume F., 2002, Adv. Synth. Catal., 344, 868, 10.1002/1615-4169(200209)344:8<868::AID-ADSC868>3.0.CO;2-M

Suárez A., 2001, Tetrahedron: Asymmetry, 12, 633, 10.1016/S0957-4166(01)00082-9

Haag D., 1998, Organometallics, 17, 398, 10.1021/om970423i

Heldmann D. K., 1999, Helv. Chim. Acta, 82, 1096, 10.1002/(SICI)1522-2675(19990707)82:7<1096::AID-HLCA1096>3.0.CO;2-I

Fache F., 2000, Chem. Rev., 100, 2159, 10.1021/cr9902897

Bedekar A. V., 1996, Tetrahedron Lett., 37, 4073, 10.1016/0040-4039(96)00736-8

Bedekar A. V., 1997, J. Org. Chem., 62, 2518, 10.1021/jo962021a

Harm A. M., 1996, Tetrahedron Lett., 37, 6189, 10.1016/0040-4039(96)01320-2

Borriello C., 2001, Tetrahedron: Asymmetry, 12, 2467, 10.1016/S0957-4166(01)00438-4