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Protecting‐Group‐Free Diastereoselective CC Coupling of 1,3‐Glycols and Allyl Acetate through Site‐Selective Primary Alcohol Dehydrogenation
Author(s) -
DechertSchmitt AnneMarie R.,
Schmitt Daniel C.,
Krische Michael J.
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.201209863
Subject(s) - dehydrogenation , alcohol , aldehyde , chemistry , primary alcohol , reagent , protecting group , iridium , organic chemistry , alcohol oxidation , primary (astronomy) , allyl alcohol , catalysis , alkyl , physics , astronomy
Safe from protection! A pronounced kinetic preference for primary alcohol dehydrogenation enables the site‐selective iridium catalyzed CC coupling of polyols with allyl acetate in the absence of protecting groups, premetallated reagents, chiral auxiliaries, and discrete alcohol‐to‐aldehyde oxidation.