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Highly Enantioselective One‐Pot Copper‐Catalyzed 1,4 Addition/Organocatalyzed α‐Substitution of Enals
Author(s) -
Quintard Adrien,
Alexakis Alexandre
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000309
Subject(s) - chemistry , stereocenter , enantioselective synthesis , copper , aldehyde , catalysis , organocatalysis , substitution (logic) , organic chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , programming language , computer science
The asymmetric copper‐catalyzed addition of dialkylzinc to enals followed by organocatalyzed one‐pot aldehyde α‐functionalization has been accomplished providing CC, CCl or CF bond formation. These simple procedures led to the creation of two contiguous stereocenters in excellent enantioselectivities (typical ee =99%). This methodology has been applied in the synthesis of (2 S ,3 S ) isomer of Valnoctamide ® .