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Catalytic Reductive Coupling of Epoxides and Aldehydes: Epoxide‐Ring Opening Precedes Carbonyl Reduction
Author(s) -
Molinaro Carmela,
Jamison Timothy F.
Publication year - 2004
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.200461705
Subject(s) - epoxide , regioselectivity , steric effects , catalysis , ring (chemistry) , chemistry , coupling (piping) , carbonyl group , reduction (mathematics) , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , geometry , mathematics , metallurgy
Several lines of evidence suggest that reduction of the carbonyl group occurs after epoxide‐ring opening in the first examples of catalytic, reductive coupling of epoxides and aldehydes (see scheme). The hydroxyether products are obtained with >95:5 regioselectivity in all cases, independent of the steric and electronic nature of R 1 and R 2 .