Chiral oxazolidinones as electrophiles: intramolecular cyclization reactions with carbanions and preparation of functionalized lactams

被引：11
|
作者：
Gibson, Sarah [1 ]
Jacobs, Hollie K. [1 ]
Gopalan, Aravamudan S. [1 ]
机构：
[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 08期
基金：
美国国家卫生研究院;
关键词：
Lactam; Chiral oxazolidinone; Intramolecular cyclization; Levetiracetam; Asymmetric synthesis; Carbanions; GLUTAMIC ACID; LEVETIRACETAM; DERIVATIVES; LITHIATION; CONCISE; AMIDES; AGENT;
D O I：
10.1016/j.tetlet.2010.12.062
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The intramolecular cyclizations of oxazolidinones with carbanions adjacent to sulfones, sulfoxides, and phosphonates proceed in high yields to obtain functionalized gamma and delta lactams. The chiral oxazolidinone precursors can be readily synthesized from commercial amino acids. The lactams from this study are useful synthetic intermediates, as demonstrated by the synthesis of a precursor for levetiracetam, an antiepileptic drug. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：887 / 890
页数：4
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