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Diarylprolinol as a Ligand for Enantioselective Alkynylation of Cyclic Imines
Author(s) -
De Munck Lode,
Monleón Alicia,
Vila Carlos,
Pedro José R.
Publication year - 2017
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.201601379
Subject(s) - chemistry , enantioselective synthesis , alkynylation , dimethylzinc , ligand (biochemistry) , catalysis , trifluoromethyl , combinatorial chemistry , methanol , diethylzinc , organic chemistry , medicinal chemistry , receptor , biochemistry , alkyl
An easily accessible prolinol derived ligand, ( S )‐bis(3,5‐bis(trifluoromethyl)phenyl)(pyrrolidin‐2‐yl)methanol, has been efficiently applied in the catalytic enantioselective addition of terminal alkynes to cyclic imines using dimethylzinc (Me 2 Zn) under mild reaction conditions. The developed catalytic system led to chiral propargylic sulfamidates with high yields (up to 97%) and excellent enantioselectivities (up to 97% ee).