手性铝(III)催化三氟甲基酮的氢膦酰化反应合成季碳 α-手性三氟甲基膦酸酯的催化不对称合成。

Catalytic asymmetric synthesis of quaternary α-hydroxy trifluoromethyl phosphonate via chiral aluminum(III) catalyzed hydrophosphonylation of trifluoromethyl ketones.

机构信息

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.

出版信息

Org Lett. 2010 Oct 1;12(19):4296-9. doi: 10.1021/ol101737b.

DOI:10.1021/ol101737b

PMID:20809651

Abstract

The chiral hydrogenated tridentate Schiff base-aluminum(III) complex has been first applied in the catalytic enantioselective hydrophosphonylation of trifluoromethyl ketones. The side reactions related to phospha-Brook rearrangement were completely avoided, and the corresponding quaternary α-hydroxy trifluoromethyl phosphonates have been first synthesized in good yields with high enantioselectivities (up to 90% ee).

摘要

手性氢化三齿席夫碱-铝（III）配合物首次应用于三氟甲基酮的催化对映选择性氢膦酰化反应。完全避免了与膦a- Brook 重排有关的副反应，首次以高产率和高对映选择性（高达 90%ee）合成了相应的季铵 α-羟基三氟甲基膦酸酯。