SEQUENTIAL DIASTEREOSELECTIVE ADDITION AND ALLYLIC AZIDE ISOMERIZATION OF SYN-ALPHA-AZIDO-BETA-(DIMETHYLPHENYLSILYL)-(E)-HEX-4-ENOATES AND ANTI-ALPHA-AZIDO-BETA-(DIMETHYLPHENYLSILYL)-(E)-HEX-4-ENOATES WITH ACETALS - ASYMMETRIC-SYNTHESIS OF GAMMA-HYDROXY-ALPHA-AMINO ACID SYNTHONS

被引：41

作者：

PANEK, JS

YANG, M

MULER, I

机构：

[1] Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, Boston

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 15期

关键词：

D O I：

10.1021/jo00041a002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

syn- and anti-methyl alpha-azido-beta-(dimethylphenylsilyl)-(E)-hex-4-enoates (2R,3R)-1a and (2S,3R)-1b undergo highly diastereo- and enantioselective addition reactions with oxonium ions catalyzed by the action of trimethylsilyl trifluoromethanesulfonate (TMSOTf) to generate alpha-azido-beta,gamma-unsaturated esters 2, with well-defined 1,4- and 1,5-stereochemical relationships, and a subsequent stereospecific allylic azide isomerization generated 1,3-azido ethers 3, synthetic equivalents of gamma-hydroxy-alpha-amino acids.

引用

页码：4063 / 4064

页数：2

共 24 条

[21] CLAISEN REARRANGEMENTS OF ENANTIOMERICALLY PURE C3-(ACYLOXY)-(E)-VINYLSILANES
SPARKS, MA
PANEK, JS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) : 3431 - 3438
[22] LIPASE MEDIATED RESOLUTION OF CHIRAL (E)-VINYLSILANES - AN IMPROVED PROCEDURE FOR THE PRODUCTION OF (R)-(E)-1-TRIALKYLSILYL-1-BUTEN-3-OL AND (S)-(E)-1-TRIALKYLSILYL-1-BUTEN-3-OL DERIVATIVES
SPARKS, MA
PANEK, JS
[J]. TETRAHEDRON LETTERS, 1991, 32 (33) : 4085 - 4088
[23] CHEMISTRY OF THE NEOPOLYOXINS, PYRIMIDINE AND IMIDAZOLINE NUCLEOSIDE PEPTIDE ANTIBIOTICS
URAMOTO, M
KOBINATA, K
ISONO, K
HIGASHIJIMA, T
MIYAZAWA, T
JENKINS, EE
MCCLOSKEY, JA
[J]. TETRAHEDRON, 1982, 38 (11) : 1599 - 1608
[24] THE REACTION OF SODIUM AZIDE WITH SOME REPRESENTATIVE EPOXIDES
VANDERWERF, CA
HEISLER, RY
MCEWEN, WE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (05) : 1231 - 1235

← 1 2 3 →