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 | Zendy

Barluenga José | Zendy; Alonso Jorge | Zendy; Fañanás Francisco J. | Zendy; Borge Javier | Zendy; GarcíaGranda Santiago | Zendy

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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.

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