Premium Intramolecular Diels–Alder Reactions: Diastereofacial Selectivity and Coupling with an Aliphatic Claisen Rearrangement
Mulzer Johann,
Bock Harald,
Eck Wolfgang,
Buschmann Jürgen,
Luger Peter
Publication year1991
Publication title
angewandte chemie international edition in english
Resource typeJournals
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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