Desymmetrization of diolefinic diols by enantioselective amino-thiocarbamate-catalyzed bromoetherification: synthesis of chiral spirocycles

Daniel Weiliang Tay; Gulice Y C Leung; Ying-Yeung Yeung

doi:10.1002/anie.201310136

Desymmetrization of diolefinic diols by enantioselective amino-thiocarbamate-catalyzed bromoetherification: synthesis of chiral spirocycles

Angew Chem Int Ed Engl. 2014 May 12;53(20):5161-4. doi: 10.1002/anie.201310136. Epub 2014 Apr 6.

Authors

Daniel Weiliang Tay¹, Gulice Y C Leung, Ying-Yeung Yeung

Affiliation

¹ Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore) http://www.chemistry.nus.edu.sg/people/academic_staff/yeungyy.htm.

PMID: 24706539
DOI: 10.1002/anie.201310136

Abstract

A facile, efficient, and highly diastereo- and enantioselective bromoetherification of diolefinic diols has been developed using an amino-thiocarbamate catalyst. Further manipulations of the bromoether products enabled entry into a new class of spirocycles which are distinctively lacking in the literature.

Keywords: Lewis base; asymmetric catalysis; chemoselectivity; cyclization; furans.