Mitsunobu Approach to the Synthesis of Optically Active α,α-Disubstituted Amino Acids

被引：73

作者：

Green, Jonathan E. ^{[1
,2
]}

Bender, David M. ^{[2
]}

Jackson, Stona ^{[2
]}

O'Donnell, Martin J. ^{[1
]}

McCarthy, James R. ^{[2
]}

机构：

[1] Indiana Univ Purdue Univ, Dept Chem & Chem Biol, Indianapolis, IN 46202 USA

[2] Eli Lilly & Co, Lilly Corp Ctr, Indianapolis, IN 46285 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 04期

关键词：

ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; ALKYL-ARYL; REAGENT; ALCOHOLS; DESIGN; ETHERS;

D O I：

10.1021/ol802325h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral tertiary alpha-hydroxy esters of known stereochemical configuration were transformed to a-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the a-carbon. Several alpha,alpha-disubstituted amino acids were synthesized in high overall chemical yield and optical purity.

引用

页码：807 / 810

页数：4

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