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Facile Synthesis of Functionally Substituted Cyclopentenones and Butenolides from Functional Vinyl Carbanions
Author(s) -
Schmidt Richard R.,
Talbiersky Jörg
Publication year - 1978
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.197802041
Subject(s) - carbanion , synthon , deprotonation , cycloaddition , chemistry , organic chemistry , catalysis , ion
A substituted C 3 synthon , the vinyl carbanion (2) , is surprisingly formed by deprotonation of the ester (1) by strong bases. Cycloaddition to (2) gives the five‐membered rings (3) and (4) , which are of significance in the synthesis of natural products.