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Enantioselective Michael Addition of Aldehydes to β‐Nitrostyrenes Catalyzed by (S)‐ N ‐(D‐Prolyl)‐1‐triflicamido‐3‐phenylpropan‐2‐amine
Author(s) -
Gorde Amol B.,
Ramapanicker Ramesh
Publication year - 2019
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.201900719
Subject(s) - chemistry , michael reaction , enantioselective synthesis , amine gas treating , organocatalysis , catalysis , organic chemistry , addition reaction , medicinal chemistry
A new organocatalyst for the asymmetric Michael addition reaction of aldehydes with β‐nitrostyrenes is developed by coupling D‐proline with (S)‐1‐triflicamido‐3‐phenylpropan‐2‐amine, which in turn is prepared from L‐phenylalaninol. The Michael addition products were obtained in very high yields (up to 93 %) and with excellent enantioselectivity (up to 97 % ee) and high diastereoselectivity (up to >99:1 dr). The catalyst is effective for reactions between α‐branched aldehydes and β‐nitrostyrenes.