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Chemoselective Multicomponent Synthesis of α,β‐Unsaturated Esters and Lactones and of Their Diels‐Alder Adducts
Author(s) -
Bestmann Hans Jürgen,
Schobert Rainer
Publication year - 1985
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.198507901
Subject(s) - adduct , chemistry , diels–alder reaction , organic chemistry , diene , catalysis , natural rubber
The “one‐pot reaction” of alcohols 1 (also chiral), aldehydes 2, and ketenylidenetriphenylphosphorane 3 yields α,β‐unsaturated esters 4 . With γ‐hydroxyaldehydes the reaction leads to formation of macrocyclic α,β‐unsaturated lactones. Four‐component reactions between 1, 2, 3 , and a diene lead immediately to Diels‐Alder adducts of 4 .