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
BANFI, L
BERNARDI, A
COLOMBO, L
GENNARI, C
SCOLASTICO, C
[J]. 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
EVANS, DA
GAUCHETPRUNET, JA
CARREIRA, EM
CHARETTE, AB
[J]. 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
HEATHCOCK, CH
YOUNG, SD
HAGEN, JP
PIRRUNG, MC
WHITE, CT
VANDERVEER, D
[J]. 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
HOWE, GP
WANG, S
PROCTER, G
[J]. 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
NICOLAOU, KC
DAINES, RA
UENISHI, J
LI, WS
PAPAHATJIS, DP
CHAKRABORTY, TK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) : 4672 - 4685
[10] SULFUR TRIOXIDE IN OXIDATION OF ALCOHOLS BY DIMETHYL SULFOXIDE
PARIKH, JR
DOERING, WVE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) : 5505 - &

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