jo500821m_si_002.cif (11.83 kB)
Nickel-Catalyzed Asymmetric Ring Opening of Oxabenzonorbornadienes with Arylboronic Acids
dataset
posted on 2014-06-06, 00:00 authored by Zhongyi Zeng, Dingqiao Yang, Yuhua Long, Xuejing Pan, Guobao Huang, Xiongjun Zuo, Wen ZhouA new, versatile,
and highly efficient nickel-catalyzed asymmetric
ring-opening (ARO) reaction of oxabenzonorbornadienes
with a wide variety of arylboronic acids has been developed, yielding cis-2-aryl-1,2-dihydronaphthalen-1-ols in high
yields (up to 99%) with good to excellent enantioselectivities (up
to 99% ee) under very mild conditions. The effects of various nickel
precursors, chiral bidentate ligands, catalyst loadings, bases, solvents,
and temperatures on the yield and enantioselectivity of the reaction
were also investigated. A plausible mechanism was proposed to account
for the formation of the corresponding cis-ring-opened
products based on the X-ray structure of product 4b.