α-(DISILYLALLENYL) α-AMINO ACID DERIVATIVES FROM THE CLAISEN REARRANGEMENT OF PROPARGYL GLYCINATES

被引：1

作者：

Mohamed, Mustafa ^{[1
]}

Brook, Michael A. ^{[1
]}

机构：

[1] McMaster Univ, Dept Chem, Hamilton, ON L8S 4M1, Canada

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2009年 / 74卷 / 06期

关键词：

Allenes; 3,3]-Sigmatropic rearrangements; Claisen rearrangement; Amino acids; Propargyl esters; STEREOCHEMICAL CONTROL; ORGANIC-SYNTHESIS; ALLENES; ESTERS;

D O I：

10.1135/cccc2009021

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Silylpropargyl glycinate esters undergo [3,3]-sigmatropic rearrangements to give 2-(disilylallenyl) glycine derivatives, interesting highly functional synthons, in moderate to good yield (30 to 85%) and in high diastereoselectivity when directed by a large silylpropargyl group (9:1 to 22:1). The highly functional amino acid, methyl (R)-2-(Boc-amino)-3,5-bis(trimethylsilyl)hexa-3,4-dienoate was isolated and characterized by X-ray crystal structure analysis.

引用

页码：927 / 934

页数：8

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