Chiral Molecular Tweezers: Synthesis and Reactivity in Asymmetric Hydrogenation

We report the synthesis and reactivity of a chiral aminoborane displaying both rapid and reversible H2 activation. The catalyst shows exceptional reactivity in asymmetric hydrogenation of enamines and unhindered imines with stereoselectivities of up to 99% ee. DFT analysis of the reaction mechanism...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2015-04, Vol.137 (12), p.4038-4041
Main Authors: Lindqvist, Markus, Borre, Katja, Axenov, Kirill, Kótai, Bianka, Nieger, Martin, Leskelä, Markku, Pápai, Imre, Repo, Timo
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We report the synthesis and reactivity of a chiral aminoborane displaying both rapid and reversible H2 activation. The catalyst shows exceptional reactivity in asymmetric hydrogenation of enamines and unhindered imines with stereoselectivities of up to 99% ee. DFT analysis of the reaction mechanism pointed to the importance of both repulsive steric and stabilizing intermolecular non-covalent forces in the stereodetermining hydride transfer step of the catalytic cycle.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja512658m