Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp3)-H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process.

Keiji MoriRyo IsogaiYuto KameiMasahiro Yamanaka Takahiko Akiyama

Published in: Journal of the American Chemical Society (2018)

Described herein is a chiral magnesium bisphosphate-catalyzed asymmetric double C(sp3)-H bond functionalization triggered by a sequential hydride shift/cyclization process. This reaction consists of stereoselective domino C(sp3)-H bond functionalization: (1) a highly enantio- and diastereoselective C(sp3)-H bond functionalization by chiral magnesium bisphosphate (first [1,5]-hydride shift), and (2) a highly diastereoselective C(sp3)-H bond functionalization by an achiral catalyst (Yb(OTf)3, second [1,5]-hydride shift).

Keyphrases

ionic liquid
room temperature
capillary electrophoresis
transition metal
electron transfer
mass spectrometry
energy transfer
carbon dioxide