Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 1, 2012
Previous Article Next Article

Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems

Author affiliations

Abstract

A general method for the synthesis of β-substituted and unsubstituted cycloheptenones bearing enantioenriched all-carbon γ-quaternary stereocenters is reported. Hydride or organometallic addition to a seven-membered ring vinylogous ester followed by finely tuned quenching parameters achieves elimination to the corresponding cycloheptenone. The resulting enones are elaborated to bi- and tricyclic compounds with potential for the preparation of non-natural analogs and whose structures are embedded in a number of cycloheptanoid natural products.

Graphical abstract: Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems

Back to tab navigation

Supplementary files

Article information


Submitted
17 Jul 2011
Accepted
27 Aug 2011
First published
01 Sep 2011

Org. Biomol. Chem., 2012,10, 56-59
Article type
Paper

Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems

N. B. Bennett, A. Y. Hong, A. M. Harned and B. M. Stoltz, Org. Biomol. Chem., 2012, 10, 56
DOI: 10.1039/C1OB06189E

Social activity

Search articles by author

Spotlight

Advertisements