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Paper | Special issue | Vol 97, No. 1, 2018, pp.493-505
Published online, 25th April, 2018
DOI: 10.3987/COM-18-S(T)41
Enantioselective Synthesis of Spiro (Isoxazole-Isoxazoline) Hybrid Ligand

Bijan Mohon Chaki, Kazuhiko Wakita, Shinobu Takizawa, Kazuhiro Takenaka, and Hiroaki Sasai*

*The Institute of Scientific and Industrial Research, Osaka University, 8-1, Mihogaoka, Ibaraki, Osaka 567-0047, Japan

Abstract

Enantioselective synthesis of chiral spiro hybrid ligand (R,S)-1 possessing isoxazole and isoxazoline rings as coordination sites was accomplished through a process involving desymmetrized intermediate 5. The key intermediate 5 was readily obtained via chiral Cu-catalyzed mono-acylation of 1,3-diol 3 or enzymatic mono-deacylation of diester 6.