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

Nathan B. Bennett, Allen Y. Hong, Andrew M. Harned, Brian M. Stoltz

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)56-59
Number of pages4
JournalOrg. Biomol. Chem.
Volume10
Issue number1
DOIs
StatePublished - 2012
Externally publishedYes

Fingerprint Dive into the research topics of 'Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems'. Together they form a unique fingerprint.

Cite this