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A Facile Cycloisomerization for the Formation of Medium and Large Rings via Allenes
Author(s) -
Trost Barry M.,
Michellys PierreYves,
Gerusz Vincent J.
Publication year - 1997
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.199717501
Subject(s) - cycloisomerization , ring (chemistry) , combinatorial chemistry , chemistry , catalysis , organic chemistry
The use of allenes as proelectrophiles in Pd‐catalyzed reaction provides a facile entry to macrocarbocycles, macrolactones, and macrolactams. Remarkably, medium‐sized rings, notoriously the most difficult to generate, are produced in excellent yields, even in preference to the more easily formed ring sizes when both are feasible (see example below).