jo402386k_si_001.pdf (1.55 MB)
Platinum(II)-Catalyzed Asymmetric Ring-Opening Addition of Arylboronic Acids to Oxabenzonorbornadienes
journal contribution
posted on 2014-01-03, 00:00 authored by Xuejing Pan, Guobao Huang, Yuhua Long, Xiongjun Zuo, Xuan Xu, Fenglong Gu, Dingqiao YangA new
platinum(II)-catalyzed asymmetric ring-opening addition of
arylboronic acids to oxabenzonorbornadienes was developed, which afforded
the corresponding cis-2-aryl-1,2-dihydronaphthalen-1-ol
products in high yields (up to 97%) with moderate to good enantioselectivities
(up to 89% ee) under very mild conditions. The effects of various
ligands, catalyst loading, bases, solvents, and temperatures on the
yield and enantioselectivity of the reaction were also investigated.
The cis configuration of product 2m was confirmed by
X-ray diffraction analysis. A potential mechanism for the present
catalytic reaction is proposed.