Enantioselective Catalysis, XIII. Preparative and Structural Chemistry of Chiral 3‐(Diphenylphosphanyl)‐pyrrolidiens and Their Palladium(II) Complexes

Wiley - Tập 130 Số 3 - Trang 385-398 - 1997
Ulrich Nagel1, Hans Günter Nedden1
1Institut für Anorganische Chemie, Universität Tübingen, Auf der Morgenstelle 18, D‐72076 Tübingen, Germany Fax: (internat.)+49(0)7071/29‐5306 E‐mail: Ulrich.Nagel@Uni‐Tuebingen.de

Tóm tắt

AbstractThe preparation of both enantiomers of 3‐diphenylphosphanulpyrrolidiine (2) and several N‐substituted derivatives together with two PdIi complexes of this ligand is reported. Form L‐malic acid and L‐hydroxyproline both enantiomers of 3‐hydroxypyrrolidine are prepared without any problems due to epimerization. KPPh2 in the presence of LiCl is shown to be the most effective reagent for the synthesis of 2. The reported X‐ray structure determination sof Pdl2 complexes show a rather rigid bicyclic hetero‐norbornane skeleton. The flexibility of the other parts of the molecules is obvious in several polymorphs revealed by this method. This polymorphism is additionally investigated by a 31P‐CP‐MAS study. From solution 1‐, 13C‐ and 31P‐NMR studies it is concluded that the bicyclic hetero‐norbornane skeleton is retained in solution.

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Tài liệu tham khảo

10.1002/ange.19840960611

10.1002/anie.198404351

10.1002/cber.19861191112

10.1002/cber.19951280316

10.1002/cber.19861190525

U.Nagel E.Kinzel J. Chem. Soc. Chem. Commun.1986 1098–1099;

10.1002/cber.19961290712

10.1021/ja00441a064

10.1021/jo00327a023

10.1021/jo00327a024

10.1021/jo01311a036

10.1021/jo00161a013

Hayashi T., Catalytic Asyummetric Synthesis, 325

10.1021/ic00056a023

P. G.Houghton G. R.Humphrey D. J.Kennedy D. C.Roberts S. H. BWright J. Chem. Soc . Perkin Trans. 11993 1421–1424.

10.1002/jlac.19677020123

Kuesters E., 1994, J. High Resoln. Chromatogr., 17, 693

H.Brunner H. J.Lautenschlager Synthesis1988 645–655;

10.1002/cber.19951280805

10.1002/prac.19040700101

10.1080/00397918508063844

10.1021/jm00040a004

10.1002/hlca.19800630118

10.1021/jo00164a027

R. M.Adlington A. G. M.Barrett P.Quayle A.Walker M. J.Betts J. Chem. Soc. Chem. Commun.1981 404–405.

10.1002/cber.19650980706

10.1002/cber.19861191112

10.1021/jo00327a023

10.1021/jo01311a036

Loupy A., 1992, Salt Effects in Organic and Organometallic Chemistry

H. G.Nedden unpublished results.

10.1002/9780470034439.ch7

Kagan H. B., 1990, The Chemistry of Organophosphorus Compounds, 52

10.1002/cber.19600930409

Noyori R., 1994, asymmetric Catalysis in Organic Synthesis, 255

10.1016/0022-328X(89)87299-7

10.1021/ic00056a023

10.1107/S0108767383001762

M. J.Potrzebowski J.Vereshchangina J.Michalski M. W.Wieczorek W.Majzner J. Chem. Soc. Dalton Trans.1995 3683–3690.

10.1002/ange.19830950505

10.1002/anie.198303901

10.1002/ange.19881000407

10.1002/anie.198804901

10.1515/znb-1981-0417

10.1016/S0022-328X(00)86030-1

10.1016/0022-2364(81)90011-1

Quin L. D., 1987, Methods in Stereochemical Analysis

Berger S., 1995, NMR Spektroskopie von Nichtmetallen

1994, HYPERCHEMTM

Harris R. K., 1964, Can. J. Chem., 42, 4475

10.1021/ja00529a042

Oki M., 1985, Methods in Stereochemical Analysis

Oki M., 1985, Methods in Stereochemical Analysis

U.Nagel H. G.Nedden Enantioselective Catalysis XIV submitted to Chem. Ber1996.

NMR READY EFERENCES CHART Aldrich 1995.

W.Kraus G.Nolze POWDER CELL 1.8 Bundesanstalt für Materialforschung und ‐prüfung D‐12205 Berlin 1995.

10.1002/9780470132487.ch51

10.1021/jo00372a038

10.1080/00397918308080895

10.1021/jm50002a006

10.1002/cber.190303602208

1995, SHELXTL V5.03