DIASTEREOSELECTION IN THE ADDITION OF ENOLATES TO CHIRAL ALPHA,BETA-EPOXYALDEHYDES

被引：22

作者：

ESCUDIER, JM ^{[1
]}

BALTAS, M ^{[1
]}

GORRICHON, L ^{[1
]}

机构：

[1] UNIV TOULOUSE 3,CNRS,SYNTHESE & PHYSICOCHIM ORGAN LAB,118 ROUTE NARBONNE,F-31062 TOULOUSE,FRANCE

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 39期

关键词：

DIASTEREOSELECTION; GAMMA; DELTA-EPOXY BETA-HYDROXYESTERS; POLYOLS; ENOLATES;

D O I：

10.1016/S0040-4039(00)92381-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemistry of addition of lithium enolates to the alpha,beta-epoxyaldehydes 1-3 has been investigated. Moderate to high diastereoselectivity (up to 13:1) is obtained in favour of the anti isomer, which is explained by the Felkin-Anh model for asymmetric induction.

引用

页码：5345 / 5348

页数：4

共 13 条

[1]

ANH NT, 1977, NOUV J CHIM, V1, P61

[2] HIGH DIASTEREOFACE SELECTION IN AN ESTER ENOLATE ADDITION TO ALPHA-ALKOXY ALDEHYDES - STEREOSELECTIVE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS [J].

BANFI, L ;

BERNARDI, A ;

COLOMBO, L ;

GENNARI, C ;

SCOLASTICO, C .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20) :3784-3790

[3]

CHEREST M, 1968, TETRAHEDRON LETT, P2199

[4] SYNTHESIS OF 1,3-DIOL SYNTHONS FROM EPOXY AROMATIC PRECURSORS - AN APPROACH TO THE CONSTRUCTION OF POLYACETATE-DERIVED NATURAL-PRODUCTS [J].

EVANS, DA ;

GAUCHETPRUNET, JA ;

CARREIRA, EM ;

CHARETTE, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :741-750

[5]

HANSON RM, 1987, J ORG CHEM, V52, P2596

[6] ACYCLIC STEREOSELECTION .9. STEREOCHEMISTRY OF THE ADDITION OF LITHIUM ENOLATES TO ALPHA-ALKOXY ALDEHYDES [J].

HEATHCOCK, CH ;

YOUNG, SD ;

HAGEN, JP ;

PIRRUNG, MC ;

WHITE, CT ;

VANDERVEER, D .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (19) :3846-3856

[7]

HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, P111

[8] STEREOSELECTIVE ADDITIONS TO ALPHA,BETA-EPOXY-ALDEHYDES - THE FORMATION OF NONCHELATION CONTROLLED PRODUCTS [J].

HOWE, GP ;

WANG, S ;

PROCTER, G .

TETRAHEDRON LETTERS, 1987, 28 (23) :2629-2632

[9] TOTAL SYNTHESIS OF AMPHOTERONOLIDE-B AND AMPHOTERICIN-B .1. STRATEGY AND STEREOCONTROLLED CONSTRUCTION OF KEY BUILDING-BLOCKS [J].

NICOLAOU, KC ;

DAINES, RA ;

UENISHI, J ;

LI, WS ;

PAPAHATJIS, DP ;

CHAKRABORTY, TK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4672-4685

[10] SULFUR TRIOXIDE IN OXIDATION OF ALCOHOLS BY DIMETHYL SULFOXIDE [J].

PARIKH, JR ;

DOERING, WVE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) :5505-&

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