Premium Intramolecular Diels–Alder Reactions: Diastereofacial Selectivity and Coupling with an Aliphatic Claisen RearrangementPremium
angewandte chemie international edition in english
Five from one! —this is the bottom line in the transformation of 1 into 4 , where one stereocenter induces four new ones. The allyl alcohol 1 is converted into the ester 2 with sorbic acid, which then cyclizes to 3 in an intramolecular Diels–Alder reaction (“CO → CC induction”). In a simple reaction sequence compound 3 opens to 4 , which contains five distinct hydroxy functions and is therefore an attractive building block for synthesis.
Subject(s)catalysis , chemistry , claisen rearrangement , diels–alder reaction , enantioselective synthesis , intramolecular force , intramolecular reaction , medicinal chemistry , organic chemistry , selectivity , stereocenter , stereochemistry
SCImago Journal Rank5.831
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