α-氟代β2-氨基酸的对映选择性合成

Enantioselective synthesis of alpha-fluorinated beta2-amino acids.

作者信息

Edmonds Michael K, Graichen Florian H M, Gardiner James, Abell Andrew D

机构信息

School of Applied Science, Christchurch Polytechnic Institute of Technology, Christchurch, New Zealand.

出版信息

Org Lett. 2008 Mar 6;10(5):885-7. doi: 10.1021/ol703045z. Epub 2008 Jan 31.

DOI:10.1021/ol703045z

PMID:18232705

Abstract

A methodology for the enantioselective synthesis of alpha-fluorinated beta2-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective fluorination and alkylation gave 7 in high diastereomeric excess (>95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active alpha-fluorinated beta2-amino acids.

摘要

已开发出一种从易得的羧酸3对α-氟化β2-氨基酸进行对映选择性合成的方法。将其转化为埃文斯恶唑烷酮，然后进行对映选择性氟化和烷基化，得到非对映体过量值高（>95%）的7。随后去除恶唑烷酮并在苄基保护的羟基中心进行胺化，得到光学活性的α-氟化β2-氨基酸。