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A Highly Efficient Synthesis of Optically Active Ferrocenylethylamines via Hydride Reduction of Chiral Ferrocenylketimines
Author(s) -
Qian Hengyu,
Yan Shihai,
Cui Xiuling,
Pi Chao,
Liu Cheng,
Wu Yangjie
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300211
Subject(s) - chemistry , optically active , hydride , absolute configuration , reduction (mathematics) , combinatorial chemistry , crystallography , stereochemistry , medicinal chemistry , organic chemistry , metal , geometry , mathematics
Due to using ( R )‐ or ( S )‐ α ‐methylbenzylamine as a chiral auxiliary, and low‐temperature regime for reduction of the intermediate ferrocenyl‐mono‐ or 1,1′‐bis‐ketimines, the corresponding secondary mono‐ or 1,1′‐bis‐amines were prepared with high diastereoselectivity. Removal of the α ‐methylbenzyl group afforded the optically active primary mono‐ and bis‐ferrocenylethylamines in high yields. The absolute configuration of ( R , R )‐ 3a and ( S , S )‐ 3b was determined by X‐ray single crystal diffraction.