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Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums toward the Synthesis of Chiral Diarylmethanes

Author:
Li, Bin, Chao, Zengyin, Li, Chunyu, Gu, Zhenhua
Source:
Journal of the American Chemical Society 2018 v.140 no.30 pp. 9400-9403
ISSN:
1520-5126
Subject:
carboxylic acids, catalysts, chemical bonding, crystal structure, enantioselectivity, models, salts, stereochemistry
Abstract:
A Cu-catalyzed enantioselective desymmetrizing ring-opening reaction of six-membered cyclic diaryliodonium salts with carboxylic acids or thioacids is reported for the facile access to chiral diarylmethanes. A Cu/[cyclopropyl bis(oxazoline)] catalyst well discriminates two C–I bonds of prochiral cyclic diaryliodonium salts. A stereochemical model was proposed to rationalize the stereochemical outcome on the basis of the crystal structure of cyclic diaryliodonium salt.
Agid:
6079159