Enantioselective protonations: fundamental insights and new concepts

Tetrahedron: Asymmetry - Tập 15 Số 23 - Trang 3653-3691 - 2004
Lucette Duhamel1, Pierre Duhamel1, Jean‐Christophe Plaquevent1
1UMR-CNRS 6014, Université de Rouen and IRCOF, Rue Tesnière, F-76821 Mont-Saint-Aignan Cedex, France

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Tài liệu tham khảo

Duhamel, 1976, C. R. Acad. Sci., 282C, 125

Duhamel, 1977, Tetrahedron Lett., 2285, 10.1016/S0040-4039(01)83742-4

Duhamel, 1978, J. Am. Chem. Soc., 100, 7415, 10.1021/ja00491a050

Duhamel, 1980, Tetrahedron Lett., 21, 2521, 10.1016/0040-4039(80)80116-X

Plaquevent, J. C. Ph. D. Thesis, Rouen, 1980

Duhamel, 1982, Bull. Soc. Chim. Fr., II, 69

Duhamel, 1982, Bull. Soc. Chim. Fr., II, 75

Duhamel, 1983, Tetrahedron Lett., 24, 4209, 10.1016/S0040-4039(00)88302-1

Duhamel, 1984, Bull. Soc. Chim. Fr., II, 421

Launay, J. C. Ph. D. Thesis, Rouen, 1986

Duhamel, 1986, Tetrahedron Lett., 27, 4975, 10.1016/S0040-4039(00)85111-4

Duhamel, 1988, Tetrahedron, 44, 5495, 10.1016/S0040-4020(01)86055-5

Duhamel, 1995, C. R. Acad. Sci., 320, 689

Duhamel, 1996, Bull. Soc. Chim. Fr., 133, 457

Duhamel, 1995, 177

Henze, 1997, Tetrahedron: Asymmetry, 8, 3363, 10.1016/S0957-4166(97)00408-4

Monteil, 2002, Mini Rev. Med. Chem., 2, 209, 10.2174/1389557023406133

Duhamel, L. unpublished results

Fehr, 1988, J. Am. Chem. Soc., 110, 6909, 10.1021/ja00228a064

Fehr, 1991, Chimia, 45, 253, 10.2533/chimia.1991.253

Fehr, 1993, Angew. Chem., Int. Ed. Engl., 32, 1042, 10.1002/anie.199310421

Fehr, 1993, Angew. Chem., Int. Ed. Engl., 32, 1044, 10.1002/anie.199310441

Fehr, 1994, Angew. Chem., Int. Ed. Engl., 33, 1888, 10.1002/anie.199418881

Fehr, 1995, J. Helv. Chim. Acta, 78, 539, 10.1002/hlca.19950780303

Fehr, 1996, Angew. Chem., Int. Ed., 35, 2566, 10.1002/anie.199625661

Fehr, 2002, Chem. Eur. J., 8, 853, 10.1002/1521-3765(20020215)8:4<853::AID-CHEM853>3.0.CO;2-5

Fuji, 1985, J. Am. Chem. Soc., 107, 6404, 10.1021/ja00308a049

Fuji, 1986, Tetrahedron Lett., 27, 5381, 10.1016/S0040-4039(00)85216-8

Fuji, 1993, Tetrahedron: Asymmetry, 4, 247, 10.1016/S0957-4166(00)82345-9

Fuji, 1995, J. Org. Chem., 60, 1914, 10.1021/jo00112a002

Gerlach, 1987, Angew. Chem., Int. Ed. Engl., 26, 1283, 10.1002/anie.198712831

Gerlach, 1988, Chemtracts, Org. Chem., I, 139

Gerlach, 1994, Chem. Ber., 127, 1969, 10.1002/cber.19941271021

Gerlach, 1994, Chem. Ber., 127, 1981, 10.1002/cber.19941271022

Gerlach, 1994, Chem. Ber., 127, 1989, 10.1002/cber.19941271023

Hünig, 1995, Vol. E 21d, 3851

Cavelier, 1993, Tetrahedron: Asymmetry, 4, 2501, 10.1016/S0957-4166(00)82229-6

Cavelier, 1994, Tetrahedron Lett., 35, 2891, 10.1016/S0040-4039(00)76652-4

Yasukata, 1993, Tetrahedron: Asymmetry, 4, 35, 10.1016/S0957-4166(00)86011-5

Koga, 1995, Synth. Org. Chem. Jpn., 53, 1021, 10.5059/yukigoseikyokaishi.53.1021

Rivière, 1997, Tetrahedron Lett., 38, 7589, 10.1016/S0040-4039(97)01790-5

Yamashita, 2000, Tetrahedron Lett., 41, 209, 10.1016/S0040-4039(99)01912-7

Hénin, 1985, Tetrahedron Lett., 26, 4945, 10.1016/S0040-4039(00)94992-X

Mortezaei, 1985, Tetrahedron Lett., 26, 6079, 10.1016/S0040-4039(00)95130-X

Mortezaei, 1986, Tetrahedron Lett., 27, 2997, 10.1016/S0040-4039(00)84700-0

Piva, 1986, Tetrahedron Lett., 27, 3001, 10.1016/S0040-4039(00)84701-2

Piva, 1987, Tetrahedron Lett., 28, 4825, 10.1016/S0040-4039(00)96635-8

Hénin, 1989, Tetrahedron, 45, 6171, 10.1016/S0040-4020(01)85129-2

Piva, 1990, J. Am. Chem. Soc., 112, 9263, 10.1021/ja00181a032

Piva, 1990, Tetrahedron Lett., 31, 5157, 10.1016/S0040-4039(00)97830-4

Hénin, 1991, New J. Chem., 15, 611

Hénin, 1991, Angew. Chem., Int. Ed. Engl., 30, 416, 10.1002/anie.199104161

Hénin, 1992, Tetrahedron: Asymmetry, 3, 1161, 10.1016/S0957-4166(00)82102-3

Muzart, 1993, Tetrahedron: Asymmetry, 4, 2531, 10.1016/S0957-4166(00)82233-8

M’Boungou-M’Passi, 1993, Bull. Soc. Chim. Fr., 130, 214

Hénin, 1994, Tetrahedron, 50, 2849, 10.1016/S0040-4020(01)86998-2

Aboulhoda, 1994, Tetrahedron: Asymmetry, 5, 1321, 10.1016/0957-4166(94)80173-8

Piva, 1994, Synlett, 729, 10.1055/s-1994-22988

Piva, 1995, J. Org. Chem., 60, 7879, 10.1021/jo00129a030

Aboulhoda, 1995, Tetrahedron: Asymmetry, 6, 1865, 10.1016/0957-4166(95)00238-K

Thorey, 1996, Tetrahedron: Asymmetry, 7, 975, 10.1016/0957-4166(96)00095-X

Muzart, 1997, Tetrahedron: Asymmetry, 8, 381, 10.1016/S0957-4166(97)84908-7

Hénin, 1997, Monatsh. Chem., 128, 1181, 10.1007/BF00807568

Aboulhoda, 1998, Tetrahedron: Asymmetry, 9, 1847, 10.1016/S0957-4166(98)00189-X

Hénin, 2000, Tetrahedron: Asymmetry, 11, 2037, 10.1016/S0957-4166(00)00151-8

Roy, 2001, Chem. Commun., 533, 10.1039/b009828k

Roy, 2002, Eur. J. Org., 3986, 10.1002/1099-0690(200212)2002:23<3986::AID-EJOC3986>3.0.CO;2-L

Roy, 2003, Tetrahedron, 59, 9641, 10.1016/j.tet.2003.09.095

Takeuchi, 1992, Bull. Chem. Soc. Jpn., 65, 2001, 10.1246/bcsj.65.2001

Takeuchi, 1994, Tetrahedron: Asymmetry, 5, 1763, 10.1016/0957-4166(94)80086-3

Nakamura, 1996, Tetrahedron: Lett., 37, 2805, 10.1016/0040-4039(96)00434-0

Nakamura, 1997, Tetrahedron: Lett., 38, 2709, 10.1016/S0040-4039(97)00435-8

Takeuchi, 1998, Tetrahedron Lett., 39, 8691, 10.1016/S0040-4039(98)01900-5

Mikami, 1998, Synlett, 607, 10.1055/s-1998-1746

Nakamura, 1999, Tetrahedron, 55, 4595, 10.1016/S0040-4020(99)00143-X

Nakamura, 2000, Tetrahedron, 56, 351, 10.1016/S0040-4020(99)01004-2

Vedejs, 1991, J. Am. Chem. Soc., 113, 5483, 10.1021/ja00014a066

Vedejs, 1994, J. Am. Chem. Soc., 116, 2175, 10.1021/ja00084a080

Vedejs, 1994, J. Org. Chem., 59, 6517, 10.1021/jo00101a008

Vedejs, 1995, J. Am. Chem. Soc., 117, 891, 10.1021/ja00108a005

Vedejs, 1998, J. Org. Chem., 63, 2792, 10.1021/jo972147n

Vedejs, 1999, J. Org. Chem., 64, 6724, 10.1021/jo990594s

Vedejs, 1999, J. Org. Chem., 64, 7863, 10.1021/jo990897m

Vedejs, 2000, J. Am. Chem. Soc., 122, 4602, 10.1021/ja994437m

Yanagisawa, 1994, Angew. Chem., Int. Ed. Engl., 33, 107, 10.1002/anie.199401071

Yanagisawa, 1994, J. Am. Chem. Soc., 116, 11179, 10.1021/ja00093a010

Yanagisawa, 1995, Synlett, 372, 10.1055/s-1995-4954

Ishihara, 1996, J. Am. Chem. Soc., 118, 12854, 10.1021/ja962414r

Yanagisawa, 1997, Synlett, 411, 10.1055/s-1997-6131

Yanagisawa, 1997, Synlett, 758

Yanagisawa, 1998, Chem. Commun., 1573, 10.1039/a803756f

Yanagisawa, 1998, Tetrahedron, 54, 10253, 10.1016/S0040-4020(98)00482-7

Yanagisawa, 1998, Synlett, 54, 174, 10.1055/s-1998-1594

Ishihara, 1998, J. Org. Chem., 63, 6444, 10.1021/jo9812936

Yanagisawa, 1999, Bull. Chem. Soc. Jpn., 72, 2337, 10.1246/bcsj.72.2337

Nakamura, 2000, J. Am. Chem. Soc., 122, 8120, 10.1021/ja001164i

Yanagisawa, 2000, J. Org. Chem., 65, 2979, 10.1021/jo991565k

Yanagisawa, 2001, Synlett, 1855, 10.1055/s-2001-18754

Ishihara, 2003, J. Am. Chem. Soc., 125, 24, 10.1021/ja021000x

Futatsugi, 2003, Chem. Commun., 566, 10.1039/b211523a

Eames, 1999, Chirality, 787, 10.1002/(SICI)1520-636X(1999)11:10<787::AID-CHIR8>3.0.CO;2-0

Eames, 2000, Tetrahedron Lett., 41, 521, 10.1016/S0040-4039(99)02109-7

Eames, 2001, Tetrahedron: Asymmetry, 12, 1, 10.1016/S0957-4166(00)00496-1

Asensio, 1998, Tetrahedron Lett., 39, 3277, 10.1016/S0040-4039(98)00469-9

Asensio, 1998, J. Org. Chem., 63, 9342, 10.1021/jo981294y

Asensio, 1998, Tetrahedron: Asymmetry, 9, 4073, 10.1016/S0957-4166(98)00426-1

Brunner, 1992, Monatsh. Chem., 123, 121, 10.1007/BF01045304

Brunner, 1996, Monatsh. Chem., 127, 845, 10.1007/BF00807023

Brunner, 2000, Z. Naturforsch., 55b, 369, 10.1515/znb-2000-0504

Brunner, 2000, Eur. J. Org. Chem., 2119, 10.1002/1099-0690(200006)2000:11<2119::AID-EJOC2119>3.0.CO;2-5

Brunner, 2000, Tetrahedron: Asymmetry, 11, 1501, 10.1016/S0957-4166(00)00091-4

Takahashi, 1996, Chem. Lett., 207, 10.1246/cl.1996.207

Takahashi, 1997, Tetrahedron: Asymmetry, 8, 3293, 10.1016/S0957-4166(97)00423-0

Kosugi, 1997, Chem. Commun., 1857, 10.1039/a704779g

Kosugi, 1997, Tetrahedron Lett., 38, 6861, 10.1016/S0040-4039(97)01618-3

Sugiura, 1997, Angew. Chem., Int. Ed., 36, 2366, 10.1002/anie.199723661

Fujihara, 1999, J. Chem. Soc., Perkin Trans., 2377, 10.1039/a901581g

Nishimura, 2001, Angew. Chem., Int. Ed., 40, 440, 10.1002/1521-3773(20010119)40:2<440::AID-ANIE440>3.0.CO;2-A

Waldmann, 1991, Nachr. Chem. Tech. Lab., 39, 413, 10.1002/nadc.19910390408

Stecher, 1987, Synthesis, 1

Pirkle, 1987, J. Am. Chem. Soc., 109, 7189, 10.1021/ja00257a047

Tsunoda, 1997, Tetrahedron Lett., 38, 7759, 10.1016/S0040-4039(97)10071-5

Tôke, 1998, Tetrahedron, 54, 213, 10.1016/S0040-4020(97)10271-X

Faber, 2001, Chem. Eur. J., 7, 5004, 10.1002/1521-3765(20011203)7:23<5004::AID-CHEM5004>3.0.CO;2-X

Trost, 1994, J. Am. Chem. Soc., 116, 10320, 10.1021/ja00101a070

Morrison, 1977

Noyori, 1994

Eliel, 1994

Potin, 1990, Angew. Chem., Int. Ed. Engl., 29, 1420, 10.1002/anie.199014201

Munoz-Muniz, 2003, Tetrahedron Lett., 44, 2023, 10.1016/S0040-4039(03)00217-X

Munoz-Muniz, 2003, Tetrahedron, 59, 4223, 10.1016/S0040-4020(03)00578-7

Calmes, 2001, Tetrahedron: Asymmetry, 12, 49, 10.1016/S0957-4166(00)00500-0

Matsumoto, 1991, Tetrahedron Lett., 32, 4729, 10.1016/S0040-4039(00)92293-7

Martin, 1997, Tetrahedron Lett., 38, 7181, 10.1016/S0040-4039(97)01705-X

Toussaint, 1987, Tetrahedron Lett., 28, 539, 10.1016/S0040-4039(00)95776-9

Carbery, 2004, Chem. Commun., 722, 10.1039/b316719d

O’Brien, 1996, Synlett, 579, 10.1055/s-1996-5488

Donohoe, 2004, Org. Lett., 6, 3055, 10.1021/ol049014q

Burton, 2000, Synlett, 22, 1640

Flinois, 2002, Tetrahedron, 58, 4707, 10.1016/S0040-4020(02)00377-0

Carey, 1977

Guetté, 1974, Tetrahedron Lett., 2409, 10.1016/S0040-4039(01)92269-5

Pirkle, 1976, Tetrahedron Lett., 2109, 10.1016/S0040-4039(00)93131-9

Capillon, 1979, Tetrahedron, 35, 1807, 10.1016/0040-4020(79)80003-4

Matsushita, 1978, Bull. Chem. Soc. Jpn., 51, 862, 10.1246/bcsj.51.862

Jackman, 1973, J. Am. Chem. Soc., 95, 3687, 10.1021/ja00792a036

Jackman, 1977, J. Am. Chem. Soc., 99, 4954, 10.1021/ja00457a011

Amstutz, 1981, Helv. Chim. Acta, 64, 2617, 10.1002/hlca.19810640819

Bauer, 1984, Helv. Chim. Acta, 67, 1972, 10.1002/hlca.19840670736

Williard, 1985, J. Am. Chem. Soc., 107, 3346, 10.1021/ja00297a049

Seebach, 1988, Angew. Chem., Int. Ed. Engl., 27, 1624, 10.1002/anie.198816241

Jackman, 1981, J. Am. Chem. Soc., 103, 4494, 10.1021/ja00405a034

Jackman, 1985, J. Am. Chem. Soc., 107, 2805, 10.1021/ja00295a042

Williard, 1987, J. Am. Chem. Soc., 109, 5541, 10.1021/ja00252a048

Loupy, 1992, Chem. Rev., 92, 1141, 10.1021/cr00014a001

Juaristi, 1993, Synthesis, 1271, 10.1055/s-1993-26041

Henderson, 1996, J. Am. Chem. Soc., 118, 1339, 10.1021/ja9527838

Abu-Hasanayn, 1996, J. Am. Chem. Soc., 118, 8136, 10.1021/ja960742l

Zerong Wang, 2000, J. Am. Chem. Soc., 122, 10754, 10.1021/ja0010002

Streitweiser, 2000, Org. Lett., 2, 3739, 10.1021/ol006650p

Kim, 2002, Org. Lett., 4, 573, 10.1021/ol017175d

Tanigushi, 1997, Tetrahedron Lett., 38, 6429, 10.1016/S0040-4039(97)01488-3

Prat, 1998, Tetrahedron: Asymmetry, 9, 2509, 10.1016/S0957-4166(98)00228-6

Zimmerman, 1987, Accounts Chem. Res., 20, 263, 10.1021/ar00139a005

Lubell, 1991, Tetrahedron: Asymmetry, 2, 543, 10.1016/S0957-4166(00)86107-8

Clericuzio, 2003, Tetrahedron: Asymmetry, 14, 119, 10.1016/S0957-4166(02)00783-8

Schmierer, 1981, Angew. Chem., Int. Ed. Engl., 20, 207, 10.1002/anie.198102071

Angibaud, 1995, Tetrahedron: Asymmetry, 6, 1919, 10.1016/0957-4166(95)00251-J

Bauer, 1984, Helv. Chim. Acta, 67, 1972, 10.1002/hlca.19840670736

Williard, 1987, J. Am. Chem. Soc., 109, 5539, 10.1021/ja00252a048

Hall, 1991, J. Am. Chem. Soc., 113, 9575, 10.1021/ja00025a024

Creger, 1970, J. Am. Chem. Soc., 92, 1396, 10.1021/ja00708a048

Pfeffer, 1972, J. Org. Chem., 37, 451, 10.1021/jo00968a027

Seebach, 1983, J. Am. Chem. Soc., 105, 5390, 10.1021/ja00354a034

Laube, 1985, Helv. Chim. Acta, 68, 1373, 10.1002/hlca.19850680530

Strazewski, 1986, Helv. Chim. Acta, 69, 1041, 10.1002/hlca.19860690512

Yamashita, 1999, Tetrahedron Lett., 40, 2803, 10.1016/S0040-4039(99)00299-3

Buschmann, 1991, Angew. Chem., Int. Ed. Engl., 30, 477, 10.1002/anie.199104771

Navarre, 2004, Angew. Chem., Int. Ed., 43, 719, 10.1002/anie.200352518

Emori, 1998, J. Am. Chem. Soc., 120, 4043, 10.1021/ja980397v

Ohtsuka, 2003, Tetrahedron: Asymmetry, 14, 967, 10.1016/S0957-4166(03)00092-2