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Dynamic Kinetic Resolution in Rhodium-Catalyzed Asymmetric Arylation of Phospholene Oxides

Author:
Lim, Kelvin Meng-Hui, Hayashi, Tamio
Source:
Journal of the American Chemical Society 2017 v.139 no.24 pp. 8122-8125
ISSN:
1520-5126
Subject:
arylation, catalysts, diastereoselectivity, enantioselectivity, isomerization, isomers, olefin, oxides, potassium hydroxide, rhodium
Abstract:
The reaction of 2,5-dihydro-1H-phosphole 1-oxide 1 with ArB(pin) 3 in the presence of a chiral (R)-segphos–rhodium catalyst under highly basic conditions (10 equiv of KOH) gave high yields of (1S,3S)-3-arylphospholane 1-oxide 4 with high diastereoselectivity as well as high enantioselectivity. Equilibration of 1 with its 2,3-dihydro isomer 2, which is chiral and racemic, by base-catalyzed olefin isomerization followed by kinetic resolution of 2 with the chiral rhodium catalyst realized the present dynamic kinetic resolution.
Agid:
6031100