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Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene OH Insertion Reaction
Author(s) -
Nicolle Simon M.,
Lewis William,
Hayes Christopher J.,
Moody Christopher J.
Publication year - 2015
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.201502484
Subject(s) - carbene , stereoselectivity , aldol reaction , intramolecular force , insertion reaction , chemistry , rhodium , medicinal chemistry , catalysis , stereochemistry , organic chemistry
Copper‐ or rhodium‐catalyzed reactions of diazocarbonyl compounds with β‐hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. Under mild conditions, the single‐step process starts as a carbene OH insertion reaction, but is diverted by an intramolecular aldol reaction.