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Title: Synthesis of chiral amines by reductive dynamic kinetic resolution
Author: Zhao, Peichao
ISNI:       0000 0004 5922 7445
Awarding Body: University of Sheffield
Current Institution: University of Sheffield
Date of Award: 2015
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Recently a heterocyclic organocatalyst for preparation of chiral imines has been developed by Jones group, for the reduction of a series of N-arylimines by trichlorosilane giving very good yield and enantioselectivities. Following previous research, this project extends the application of the organocatalyst 117 for preparation of chiral amines with two stereogenic centers by reductive dynamic or kinetic resolution. Reduction of the imine derived from 2-phenylpropionaldehyde suffered a competitive background reaction without catalyst giving racemic product. In terms of asymmetric reduction of 2-substituted imines, both 2-methylcyclohexanone imine and 2-methyltetralone imine gave moderate yields (51%) and enantioselectivities (25%). A number of imines of 3-substituted indanone were reduced using only 1 mol% catalyst by trichlorosilane giving the corresponding chiral amines with good yields (10-65%), excellent enantioselectivities (80-96%) and diastereoselectivities (up to 90:1).
Supervisor: Jones, Simon Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available