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Intramolecular Diels–Alder Reactions: Diastereofacial Selectivity and Coupling with an Aliphatic Claisen Rearrangement
Author(s) -
Mulzer Johann,
Bock Harald,
Eck Wolfgang,
Buschmann Jürgen,
Luger Peter
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199104141
Subject(s) - stereocenter , intramolecular force , claisen rearrangement , chemistry , diels–alder reaction , selectivity , stereochemistry , intramolecular reaction , organic chemistry , enantioselective synthesis , catalysis
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.