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Highly Stereoselective aza‐Baylis–Hillman Reactions of CF 3 ‐Sulfinylimines: Straightforward Access to α‐Methylene β‐CF 3 β‐Amino Acids
Author(s) -
Milcent Thierry,
Hao Jing,
Kawada Kosuke,
Soloshonok Vadim A.,
Ongeri Sandrine,
Crousse Benoit
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402078
Subject(s) - chemistry , methylene , stereoselectivity , octane , michael reaction , stereochemistry , amino acid , baylis–hillman reaction , organocatalysis , dabco , catalysis , enantioselective synthesis , medicinal chemistry , combinatorial chemistry , organic chemistry , biochemistry
1,4‐Diazabicyclo[2.2.2]octane‐catalyzed asymmetric aza‐Baylis–Hillman (ABH) reaction of ( R )‐ N ‐ tert ‐butanesulfinyl‐(3,3,3)‐trifluoroacetaldimine with various Michael acceptors proceeds with exceptionally high rates and stereochemical outcome. This ABH approach provides convenient and practical access to previously unknown enantiomerically pure α‐methylene β‐CF 3 β‐amino esters/acids, forthright useable for peptide synthesis.