Asymmetric synthesis of A-240610.0 via a new atropselective approach for axially chiral biaryls with chirality transfer.
A new approach for atropselective preparation of axially chiral biaryl was developed. This process proceeded through a chirality transfer from a stereogenic center of a secondary alcohol to the stereogenic axis via regioselective intramolecular silyl group migration. This methodology allowed for the preparation of a single atropisomer 2 in good yield (85%) with high diastereoselectivity (99:1), which subsequently led to the successful development of an efficient asymmetric synthesis of A-240610.0, 1.
Ku
Yi-Yin
YY
D-R450, Process Chemistry, Global Pharmaceutical Research and Development, Abbott Laboratories, North Chicago, Illinois 60064-4000, USA. yiyin.ku@abbott.com
Grieme
Tim
T
Raje
Prasad
P
Sharma
Padam
P
King
Steve A
SA
Morton
Howard E
HE
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis*; D005938:Glucocorticoids / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D013237:Stereoisomerism
C456759:A-240610; D000894:Anti-Inflammatory Agents, Non-Steroidal; D005938:Glucocorticoids; D006576:Heterocyclic Compounds, 4 or More Rings