A Simple Metal-Promoted Three-Step Access to n/5/m Angular Carbocyclic Systems | Zendy

José Barluenga | Zendy; Ana ÁlvarezFernández | Zendy; Tatiana SuárezRodríguez | Zendy; A.L. Suarez-Sobrino | Zendy; Miguel Tomás | Zendy

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A Simple Metal-Promoted Three-Step Access to n/5/m Angular Carbocyclic Systems

Author(s) -

José Barluenga,

Ana ÁlvarezFernández,

Tatiana SuárezRodríguez,

A.L. Suarez-Sobrino,

Miguel Tomás

Publication year - 2013

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol303269r

Subject(s) - chemistry , propargyl , annulation , tin , metal , stereochemistry , catalysis , fragmentation (computing) , medicinal chemistry , combinatorial chemistry , organic chemistry , operating system , computer science

A simple three-step access to n/5/m angular tricyclic skeleta from terminal cycloalkenylacetylenes, Cr(CO)(6), and propargylmalonate esters is described. The process involves a cyclopentannulation of propargylmalonates and enynyl Fischer carbenes, followed by a metal-promoted Cope-type fragmentation of the propargyl unit. The resulting 4-allenyl-carbonyl derivatives can undergo either a 5-exo annulation via a tin enolate or an unprecedented gold catalyzed 6-endo cyclization.

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