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C 2 ‐Symmetric Bicyclic Bisborane Catalysts: Kinetic or Thermodynamic Products of a Reversible Hydroboration of Dienes
Author(s) -
Tu XianShuang,
Zeng NingNing,
Li RuYe,
Zhao YuQuan,
Xie DeZhen,
Peng Qian,
Wang XiaoChen
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201808289
Subject(s) - hydroboration , bicyclic molecule , chemistry , catalysis , diastereomer , imine , borane , kinetic energy , medicinal chemistry , diene , organic chemistry , stereochemistry , physics , natural rubber , quantum mechanics
We prepared a new class of chiral C 2 ‐symmetric bicyclic bisborane catalysts by addition reactions of internal dienes with the Piers borane, HB(C 6 F 5 ) 2 , and an analogue, HB( p ‐C 6 F 4 H) 2 . The dependence of the addition pattern on the reaction temperature allowed us to selectively prepare two diastereomeric catalysts from a single diene precursor. The bisboranes prepared in situ exhibited excellent activity (turnover numbers up to 200 at −40 °C) and enantioselectivity (up to 95 % ee ) in imine hydrogenation reactions.