CHIRAL GAMMA-SILYLOXY ALLYLSTANNANES AS SYNTHETIC REAGENTS - PROOF OF ABSOLUTE-CONFIGURATION

被引：17

作者：

MARSHALL, JA

WELMAKER, GS

机构：

[1] Department of Chemistry, The University of South Carolina, Columbia

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 19期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)71247-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

gamma-Silyloxy allylstannanes can be prepared directly from alpha-hydroxy allylstannanes by treatment with TBSOTf and (i-Pr)2NEt in CH2Cl2. The attendant 1,3-isomerization proceeds by an anti pathway as shown by comparison of the absolute configuration of reactant and product.

引用

页码：2101 / 2104

页数：4

共 18 条

[1] ASYMMETRIC REDUCTION OF ACYLSTANNANES - PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-ALKOXYSTANNANES
CHAN, PCM
CHONG, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) : 5584 - 5586
[2] FILLIPO JS, 1981, J AM CHEM SOC, V103, P5588
[3] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION
GAO, Y
HANSON, RM
KLUNDER, JM
KO, SY
MASAMUNE, H
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) : 5765 - 5780
[4] GONELLA NC, 1982, J AM CHEM SOC, V104, P3775
[5] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF OPTICALLY-ACTIVE E-1-ALKOXYMETHOXY-BUT-2-ENYL(TRI-N-BUTYL)STANNANES - STEREOSELECTIVE REACTIONS WITH ALDEHYDES
JEPHCOTE, VJ
PRATT, AJ
THOMAS, EJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (12) : 800 - 802
[6] NEW ALLYLSTANNANES FOR THE CONNECTIVE CONSTRUCTION OF MONOPROTECTED VICINAL DIOLS
KECK, GE
ABBOTT, DE
WILEY, MR
[J]. TETRAHEDRON LETTERS, 1987, 28 (02) : 139 - 142
[7] STEREOSELECTIVE ACYCLIC SYNTHESIS VIA ALLYLMETALS - THREO VICINAL DIOLS FROM BOTH E-GAMMA-ALKOXYALLYLTINS AND Z-GAMMA-ALKOXYALLYLTINS AND ALDEHYDES
KOREEDA, M
TANAKA, Y
[J]. TETRAHEDRON LETTERS, 1987, 28 (02) : 143 - 146
[8] ENANTIOMERICALLY ENRICHED ALLYLSTANNANES FROM CHIRAL ALLYLLITHIUM DERIVATIVES AND THEIR HIGHLY REGIOSELECTIVE, DIASTEREOSELECTIVE AND ENANTIOSELECTIVE HYDROXYALKYLATION
KRAMER, T
SCHWARK, JR
HOPPE, D
[J]. TETRAHEDRON LETTERS, 1989, 30 (50) : 7037 - 7040
[9] ON THE 1,3-ISOMERIZATION OF NONRACEMIC ALPHA-(ALKOXY)ALLYLSTANNANES
MARSHALL, JA
GUNG, WY
[J]. TETRAHEDRON LETTERS, 1989, 30 (52) : 7349 - 7352
[10] CEMBRANOLIDE TOTAL SYNTHESIS - MACROCYCLIZATION OF (ALPHA-ALKOXYALLYL)STANNANE ACETYLENIC ALDEHYDES AS A ROUTE TO CEMBRANE LACTONES
MARSHALL, JA
CROOKS, SL
DEHOFF, BS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) : 1616 - 1623

← 1 2 →