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[3+3] Cyclizations of 1,3‐Bis(silyl enol ether)s with 1,1‐Diacetylcyclopentane and 1,1‐Diacetylcyclopropane
Author(s) -
Langer Peter,
Bose Gopal
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351263
Subject(s) - silylation , domino , chemistry , silyl enol ether , enol , silyl ether , ether , natural product , organic chemistry , combinatorial chemistry , medicinal chemistry , stereochemistry , catalysis
Domino reactions of 1,3‐bis(silyl enol ether)s with 1,1‐diacetylcyclopentane and 1,1‐diacetylcyclopropane (see scheme) allow a new and convenient one‐pot synthesis of spiro[5.4]cyclodecenones, bicyclo[4.4.0]deca‐1,4‐dien‐3‐ones, and functionalized salicylates, which are versatile intermediates for the synthesis of pharmacologically relevant natural product analogues. MS=molecular sieves.