DIASTEREOSELECTIVITY ENHANCEMENT IN VINYLCUPRATE ADDITION TO BETA-ALKOXYALDEHYDES VIA A VINYLSILANE

被引：15

作者：

BURKE, SD

PISCOPIO, AD

MARRON, BE

MATULENKO, MA

PAN, G

机构：

[1] Department of Chemistry, University of Wisconsin-Madison, Madison

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 07期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)92104-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The presence of a removable 1-(trimethylsilyl) residue greatly increases the chelation-controlled diastereoselectivity in alkenylcuprate additions to chiral beta-alkoxyaldehydes. Several methods for protiodesilylation of the resultant allylic alcohols [5 --> 2b (R = Me3SiCH2CH2OCH2-, PhCH2OCH2-, and PhCH2-)T are compared.

引用

页码：857 / 858

页数：2

共 10 条

[1] Boeckman R. K., 1978, ORG SYNTH, V58, P152
[2] 1-(TRIMETHYLSILYL)BENZENE OXIDES - SYNTHESIS, AROMATIZATION, AND REACTIONS OF CARBANIONS FROM DESILYLATION
BOYD, DR
BERCHTOLD, GA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (03) : 468 - 470
[3] STEREOCONTROLLED ONE-POT CONVERSIONS OF ALPHA-ALKOXY ESTERS TO SYN-1,2-DIOL AND ANTI-1,2-DIOL DERIVATIVES
BURKE, SD
DEATON, DN
OLSEN, RJ
ARMISTEAD, DM
BLOUGH, BE
[J]. TETRAHEDRON LETTERS, 1987, 28 (34) : 3905 - 3906
[4] CHAN TH, 1974, TETRAHEDRON LETT, P3479
[5] 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
[6] ALPHA-CHELATION CONTROLLED NUCLEOPHILIC-ADDITION TO CHIRAL ALPHA, BETA-DIALKOXY CARBONYL-COMPOUNDS - DIASTEREOSELECTIVE PREPARATION OF L-XYLO AND L-LYXO TRIOLS
IIDA, H
YAMAZAKI, N
KIBAYASHI, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) : 3769 - 3771
[7] BETA-(TRIMETHYLSILYL)ETHOXYMETHYL CHLORIDE - A NEW REAGENT FOR THE PROTECTION OF THE HYDROXYL GROUP
LIPSHUTZ, BH
PEGRAM, JJ
[J]. TETRAHEDRON LETTERS, 1980, 21 (35) : 3343 - 3346
[8] BASE-CATALYZED REARRANGEMENT OF BETA-HYDROXYVINYLSILANES TO ALLYL SILYL ETHERS
SATO, F
TANAKA, Y
SATO, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (04) : 165 - 166
[9] STILL WC, 1980, TETRAHEDRON LETT, V21, P1031
[10] STILL WC, 1980, TETRAHEDRON LETT, V21, P1035

← 1 →