Highly Diastereoselective Indium-Mediated Allenylation of N-tert-Butanesulfinyl Imino Ester: Efficient Synthesis of Optically Active α-Allenylglycines

被引：30
|
作者：
Jin, Shen-Shuang [1 ]
Xu, Ming-Hua [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 18期
基金：
中国国家自然科学基金;
关键词：
allenylation; alpha-allenylglycine; N-tert-butanesulfinyl imino ester; indium; cis-substituted proline; CONCISE ASYMMETRIC-SYNTHESIS; AMINO-ACIDS; BIS(SULFINYL)IMIDOAMIDINE LIGANDS; STEREOSELECTIVE-SYNTHESIS; CATALYZED-REACTIONS; VICINAL DIAMINES; ALLENES; REARRANGEMENT; CYCLIZATION; ALLYLATION;
D O I：
10.1002/adsc.201000688
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient and practical asymmetric synthesis of highly enantiomerically enriched alpha-allenylglycines by room temperature indium-mediated allenylation of chiral N-tert-butanesulfinyl imino esters with propargylic halides is described. The synthetic utilities of the approach were demonstrated by the rapid and convenient preparation of challenging cis-substituted proline derivatives.
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页码：3136 / 3140
页数：5
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