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Diastereoselective Synthesis of Cycloheptadienol Derivatives by a Formal [5+2] Carbocyclization Reaction of α,β,γ,δ‐Diunsaturated (Methoxy)carbene Complexes with Methyl Ketone Lithium Enolates
Author(s) -
Barluenga José,
Alonso Jorge,
Fañanás Francisco J.,
Borge Javier,
GarcíaGranda Santiago
Publication year - 2004
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.200460547
Subject(s) - lithium (medication) , ketone , carbene , formal synthesis , chemistry , methyl ketone , medicinal chemistry , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , medicine , endocrinology
Magnificent seven! Functionalized seven‐membered carbocycles can be easily synthesized in a diastereoselective way by a formal [5+2] carbocyclization reaction from dienylmethoxycarbene complexes and methyl ketone lithium enolates (see scheme). Examples for R: Ph, 2‐Fu, PhCH 2 CH 2 , TMSCC; R 1 : H, Me; R 2 : Ph, 2‐Fu are presented.