1,3-ASYMMETRIC INDUCTION IN THE ALDOL ADDITION-REACTIONS OF METHYL KETONE ENOLATES AND ENOLSILANES TO BETA-SUBSTITUTED ALDEHYDES - A MODEL FOR CHIRALITY TRANSFER

被引：116

作者：

EVANS, DA

DUFFY, JL

DART, MJ

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(00)78430-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direction and degree of 1,3-asymmetric induction have been evaluated in the addition of metal enolates and enolsilanes to aldehydes substituted at the beta position with both polar (OR, OAc, Cl) and nonpolar (Me) substituents. A model for 1,3-asymmetric induction for polar addition processes such as the Mukaiyama aldol reaction is proposed to account for the documented trends in reaction diastereoselection for polar beta-substituents.

引用

页码：8537 / 8540

页数：4

共 31 条

[1] METHODOLOGY TO ESTABLISH 1,2-DIFUNCTIONALITY AND 1,3-DIFUNCTIONALITY FOR THE SYNTHESIS OF CARBOHYDRATE-DERIVATIVES
AGER, DJ
EAST, MB
[J]. TETRAHEDRON, 1992, 48 (14) : 2803 - 2894
[2] Ahn N. T., 1977, NOUV J CHIM, V1, P61
[3] STEREOCONTROL IN THE MUKAIYAMA ALDOL ADDITION TO CHIRAL ALPHA-THIO SUBSTITUTED AND BETA-THIO-SUBSTITUTED ALDEHYDES
ANNUNZIATA, R
CINQUINI, M
COZZI, F
COZZI, PG
CONSOLANDI, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) : 456 - 461
[4] 1,2-ANTI DIASTEREOSELECTIVE REDUCTION OF 2-ALKYL-3-HYDROXY-KETONES VIA THEIR SILYL ETHERS
BLOCH, R
GILBERT, L
GIRARD, C
[J]. TETRAHEDRON LETTERS, 1988, 29 (09) : 1021 - 1024
[5] BRIENNE MJ, 1968, B SOC CHIM FR, P1036
[6] CHELATES AS INTERMEDIATES IN NUCLEOPHILIC ADDITIONS TO ALKOXY KETONES ACCORDING TO CRAM RULE (CYCLIC MODEL)
CHEN, XN
HORTELANO, ER
ELIEL, EL
FRYE, SV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1778 - 1784
[7] CHEREST M, 1968, TETRAHEDRON LETT, P2199
[8] STUDIES IN STEREOCHEMISTRY .30. MODELS FOR STERIC CONTROL OF ASYMMETRIC INDUCTION
CRAM, DJ
KOPECKY, KR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (11) : 2748 - 2755
[9] ACYCLIC DIASTEREOSELECTION IN THE HYDROBORATION PROCESS - DOCUMENTED CASES OF 1,3-ASYMMETRIC INDUCTION
EVANS, DA
BARTROLI, J
GODEL, T
[J]. TETRAHEDRON LETTERS, 1982, 23 (44) : 4577 - 4580
[10] EVANS DA, 1994, TETRAHEDRON LETT, V35

← 1 2 3 4 →