α,β-不饱和酰基恶唑烷酮的共轭三氟甲基化反应：手性氟化氨基酸的合成。

Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: synthesis of chiral fluorinated amino acids.

机构信息

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, D-14195 Berlin, Germany.

出版信息

Org Biomol Chem. 2012 Nov 21;10(43):8583-6. doi: 10.1039/c2ob26810h.

Abstract

A novel conjugate hydrofluoroalkylation of α,β-unsaturated acyl-oxazolidinones is described. Using this method, enantiomerically pure β-trifluoromethylated amino acids were prepared. Trifluorovaline and trifluoroisoleucine were incorporated into peptides and found to show extremely low α-helix propensities.

摘要

描述了一种新颖的α，β-不饱和酰基恶唑烷酮的共轭氢氟烷基化反应。利用该方法，制备了对映体纯的β-三氟甲基化氨基酸。将三氟缬氨酸和三氟异亮氨酸掺入到肽中，发现它们具有极低的α-螺旋倾向。