Synthesis of enantiomerically enriched β-amino alcohol derivatives via asymmetric lithiation of O-benzyl carbamates-imine addition using (-)-sparteine complexes

被引：13

作者：

Arrasate, S ^{[1
]}

Lete, E ^{[1
]}

Sotomayor, N ^{[1
]}

机构：

[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ 2, E-48080 Bilbao, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(02)00078-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric lithiation of O-benzyl carbamates-imine addition sequence using sec-butyllithium/(-)-sparteine complexes has been studied. The reactions proceed with high diastereoselectivity, giving the threo beta-amino alcohol derivatives with modest to good e.e. The best enantioinduction was obtained with O-benzyl carbamates bearing methoxy substituents on the aromatic ring. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：311 / 316

页数：6

共 47 条

[21] Heteroatom-directed lithiations of chiral alkyl carbamates: A powerful tool for enantioselective synthesis [J].

Hoppe, D ;

Ahrens, H ;

Guarnieri, W ;

Helmke, H ;

Kolczewski, S .

PURE AND APPLIED CHEMISTRY, 1996, 68 (03) :613-618

[22] ENANTIOSELECTIVE SYNTHESIS VIA SPARTEINE-INDUCED ASYMMETRIC DEPROTONATION [J].

HOPPE, D ;

HINTZE, F ;

TEBBEN, P ;

PAETOW, M ;

AHRENS, H ;

SCHWERDTFEGER, J ;

SOMMERFELD, P ;

HALLER, J ;

GUARNIERI, W ;

KOLCZEWSKI, S ;

HENSE, T ;

HOPPE, I .

PURE AND APPLIED CHEMISTRY, 1994, 66 (07) :1479-1486

[23] CHIRAL LITHIUM-1-OXYALKANIDES BY ASYMMETRIC DEPROTONATION - ENANTIOSELECTIVE SYNTHESIS OF 2-HYDROXYALKANOIC ACIDS AND SECONDARY ALKANOLS [J].

HOPPE, D ;

HINTZE, F ;

TEBBEN, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (12) :1422-1424

[24] GENERATION OF A CONFIGURATIONALLY STABLE CHIRAL BENZYLLITHIUM DERIVATIVE, AND THE CAPRICIOUS STEREOCHEMISTRY OF ITS ELECTROPHILIC SUBSTITUTION [J].

HOPPE, D ;

CARSTENS, A ;

KRAMER, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (12) :1424-1425

[25] Studies aimed at enhancement of reactivity and enantioselectivity of a lithium ester enolate using a chiral tridentate lithium amide [J].

Hussein, MA ;

Iida, A ;

Tomioka, K .

TETRAHEDRON, 1999, 55 (37) :11219-11228

[26]

Keyserlingk N.G., 2002, Eur. J. Org. Chem, P301

[27] Stereoselective synthesis of trans-4,5-disubstituted 1,3-imidazolidin-2-ones by reaction of an alpha-nitrogen carbanion with imines [J].

Kise, N ;

Kashiwagi, K ;

Watanabe, M ;

Yoshida, JI .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :428-429

[28]

Kleinman E.F.V., 1991, COMPREHENSIVE ORGA 2, V2

[29]

KLIN J, 1989, CHEM DOUBLE BON 1 SA, V2

[30] Catalytic enantioselective addition to imines [J].

Kobayashi, S ;

Ishitani, H .

CHEMICAL REVIEWS, 1999, 99 (05) :1069-1094

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