Synthesis 2019; 51(13): 2713-2719
DOI: 10.1055/s-0037-1611533
special topic
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of 2-Substituted Pyrrolidines via Intramolecular­ Reductive Amination

Huan Zhou
,
Wenlei Zhao
,
Tao Zhang
,
Haodong Guo
,
Haizhou Huang*
,
Financial support from the National Natural Science Foundation of China (21772155, 21402155 and 21602172) is gratefully acknowledged.
Further Information

Publication History

Received: 19.03.2109

Accepted after revision: 12 April 2019

Publication Date:
07 May 2019 (eFirst)

Published as part of the Special Topic Amination Reactions in Organic Synthesis

Abstract

Catalyzed by the complex generated in situ from iridium and the chiral ferrocene ligand, tert-butyl (4-oxo-4-arylbutyl)carbamate substrates were deprotected and then reductively cyclised to form 2-substituted arylpyrrolidines in a one-pot manner, in which the intramolecular reductive amination was the key step. A range of chiral 2-substituted arylpyrrolidines were synthesised in up to 98% yield and 92% ee.

Supporting Information

 
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