Selective Access to E- and Z-螖Ile-Containing Peptides via a Stereospecific E2 Dehydration and an O 鈫?N Acyl Transfer
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- 作者：Zhiwei Ma ; Jintao Jiang ; Shi Luo ; Yu Cai ; Joseph M. Cardon ; Benjamin M. Kay ; Daniel H. Ess ; Steven L. Castle
- 刊名：Organic Letters
- 出版年：2014
- 出版时间：August 1, 2014
- 年：2014
- 卷：16
- 期：15
- 页码：4044-4047
- 全文大小：337K
- ISSN：1523-7052
文摘
A concise synthesis of peptides that contain E- or Z-dehydroisoleucine (螖Ile) residues is reported. The key reaction is an unusual anti dehydration of 尾-tert-hydroxy amino acid derivatives that is mediated by the Martin sulfurane. A subsequent tandem Staudinger reduction鈥揙 鈫?N acyl transfer process forges an amide bond to the 螖Ile residue with minimal E/Z alkene isomerization. Density functional calculations attribute the stereospecific dehydration to a highly asynchronous E2 anti process.