Highly diastereoselective aldol additions of a chiral ethyl ketone enolate under Lewis base catalysis

被引：18

作者：

Denmark, SE ^{[1
]}

Pham, SM ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 14期

关键词：

D O I：

10.1021/ol0160497

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The aldol addition of a chiral ethyl ketone enolate bearing an oxygen substituent (OTBS) at the alpha -position proceeds with high internal and relative diastereoselectivities with various achiral aldehydes in good yields, The profound influence of the resident stereogenic center allows for the use of an achiral catalyst, such as HMPA, with minor attenuation in internal stereoselectivity,

引用

页码：2201 / 2204

页数：4

共 28 条

[1]

[Anonymous], 1997, ORG REACT

[2]

BRAUN M, 1996, STEREOSELECTIVE SYNT, V3, P1612

[3] ARE CHELATES TRULY INTERMEDIATES IN CRAMS CHELATE RULE [J].

CHEN, XN ;

HORTELANO, ER ;

ELIEL, EL ;

FRYE, SV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (16) :6130-6131

[4] STUDIES WITH TRIALKYLSILYLTRIFLATES - NEW SYNTHESES AND APPLICATIONS [J].

COREY, EJ ;

CHO, H ;

RUCKER, C ;

HUA, DH .

TETRAHEDRON LETTERS, 1981, 22 (36) :3455-3458

[5]

Denmark S. E., UNPUB

[6]

Denmark S. E., 2000, MODERN CARBONYL CHEM

[7]

Denmark SE, 2001, SYNLETT, P1024

[8] The chemistry of trichlorosilyl enolates. 6. Mechanistic duality in the Lewis base-catalyzed aldol addition reaction [J].

Denmark, SE ;

Su, XP ;

Nishigaichi, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :12990-12991

[9] Chiral phosphoramide-catalyzed aldol additions of ketone enolates. Preparative aspects [J].

Denmark, SE ;

Stavenger, RA ;

Wong, KT ;

Su, XP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) :4982-4991

[10] Synthesis of phosphoramides for the Lewis base-catalyzed allylation and aldol addition reactions [J].

Denmark, SE ;

Su, YP ;

Nishigaichi, Y ;

Coe, DM ;

Wong, KT ;

Winter, SBD ;

Choi, JY .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :1958-1967

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