Diastereospecific nazarov cyclization of fully substituted dienones: generation of vicinal all-carbon-atom quaternary stereocenters

Anais Jolit; Saleta Vazquez-Rodriguez; Glenn P A Yap; Marcus A Tius

doi:10.1002/anie.201305218

Diastereospecific nazarov cyclization of fully substituted dienones: generation of vicinal all-carbon-atom quaternary stereocenters

Angew Chem Int Ed Engl. 2013 Oct 11;52(42):11102-5. doi: 10.1002/anie.201305218. Epub 2013 Sep 3.

Authors

Anais Jolit¹, Saleta Vazquez-Rodriguez, Glenn P A Yap, Marcus A Tius

Affiliation

¹ Chemistry Department, University of Hawaii at Manoa, 2545 The Mall, Honolulu, HI 96822 (USA).

Abstract

No vacancy: Fully substituted dienones that are highly polarized by a vinylogous carbonate group were found to undergo a remarkably rapid and diastereospecific Nazarov cyclization that led to cyclopentenones with vicinal all-carbon-atom quaternary centers (see example; SEM=2-(trimethylsilyl)ethoxymethyl, Tf=trifluoromethanesulfonyl).

Keywords: Nazarov cyclization; diastereoselectivity; quaternary stereocenters; rearrangement; synthetic methods.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkenes / chemistry*
Cyclization
Cyclopentanes / chemical synthesis*
Ketones / chemical synthesis
Ketones / chemistry*
Stereoisomerism

Substances

Alkenes
Cyclopentanes
Ketones

Abstract

Publication types

MeSH terms

Substances

Grants and funding