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Formal Enantioselective Hydroamination of Non‐Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1‐Phenylethylamines in Chemoenzymatic One‐Pot Synthesis
Author(s) -
Uthoff Florian,
Sato Hirofumi,
Gröger Harald
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201601463
Subject(s) - hydroamination , enantioselective synthesis , transamination , alkene , chemistry , catalysis , combinatorial chemistry , organic chemistry , substrate (aquarium) , amination , formal synthesis , enzyme , oceanography , geology
As a complementary approach to current asymmetric synthetic methods, a direct transformation of styrenes into 1‐phenylethylamines was developed. The one‐pot process represents a formal hydroamination of a non‐activated alkene with ammonia and is based on the combination of a Pd/Cu‐catalyzed Wacker‐oxidation with an enzymatic transamination. A key feature of this process is the compartmentation of the catalytic systems, which turned out to be essential to avoid deactivation of the transaminase by the Cu‐component. This one‐pot synthesis can be applied to a broad substrate range, which leads to the chiral amines with high conversions and excellent enantioselectivities of >99 % ee .