Tetramic acids and derivatives by telluride-triggered Dieckmann cyclizations

被引：14

作者：

Dittmer, Donald C. ^{[1
]}

Avilov, Dmitry V. ^{[1
]}

Kandula, Venkata Subbarao ^{[1
]}

Purzycki, Matthew T. ^{[1
]}

Martens, Zachary J. ^{[1
]}

Hohn, Elliot B. ^{[1
]}

Bacler, Matthew W. ^{[1
]}

机构：

[1] Syracuse Univ, Dept Chem, Room 1-014 CST, Syracuse, NY 13244 USA

来源：

ARKIVOC | 2010年

关键词：

Tetramic acids; lithium telluride; alpha-bromoacyl amino acid esters; crown ether; racemization of silyl enol ethers; enol tosylates; SOLID-PHASE SYNTHESIS; PYRROLIZIDINE RING-SYSTEM; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; ASYMMETRIC-SYNTHESIS; POTENT INHIBITORS; TETRONIC ACIDS; LEWIS-ACID; CHEMISTRY; EFFICIENT;

D O I：

10.3998/ark.5550190.0011.608

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of alpha-bromoacyl amides of esters of N-protected alpha-amino acids with lithium telluride yields an amide enolate which cyclizes to unstable tetramic acids (2, 4-pyrrolidinediones) which can be converted to stable derivatives (e.g. enol esters, silyl enol ethers, enol tosylates). Reaction conditions are modified to reduce unwanted side reactions: protonation of the enolate, self-catalyzed intermolecular aldol rections of the tetramic acids, and potential racemization at the alpha-carbon atom of the amino acid.

引用

页码：61 / 83

页数：23

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