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Diisopinocampheylborane‐Mediated Reductive Aldol Reactions: Highly Enantio‐ and Diastereoselective Synthesis of syn Aldols from N ‐Acryloylmorpholine
Author(s) -
Nuhant Philippe,
Allais Christophe,
Roush William R.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201302535
Subject(s) - aldol reaction , hydroboration , chemistry , alkyl , stereochemistry , aryl , organic chemistry , catalysis
Cutting costs, cutting corners : In an inexpensive and straightforward synthesis of syn ‐propionamide aldols, formation of the Z enolborinate by the hydroboration of 4‐acryloylmorpholine with diisopinocampheylborane ((Ipc) 2 BH) was followed by aldol reactions with achiral and chiral aldehydes to provide syn ‐α‐methyl‐β‐hydroxymorpholinecarboxamides with excellent enantio‐ and diastereoselectivity (see scheme; R=alkyl, alkenyl, aryl, heteroaryl).