Synthesis 2015; 47(10): 1488-1498
DOI: 10.1055/s-0034-1380163
paper
© Georg Thieme Verlag Stuttgart · New York

A Mild Protocol for the Regioselective Ring Opening of Doubly Activated Cyclopropanes by Using Selenolates Generated in Situ: Synthesis of Functionalized Organoselenium Compounds

Purushothaman Gopinath
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India   Email: scn@orgchem.iisc.ernet.in
,
R. N. Chandrakala
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India   Email: scn@orgchem.iisc.ernet.in
,
Srinivasan Chandrasekaran*
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India   Email: scn@orgchem.iisc.ernet.in
› Author Affiliations
Further Information

Publication History

Received: 02 August 2014

Accepted after revision: 21 January 2015

Publication Date:
27 February 2015 (online)


Abstract

A variety of functionalized organoselenium compounds were synthesized from doubly activated cyclopropanes and diselenides in the presence of sodium borohydride. A range of substituents were stable under these reaction conditions. Additionally, we extended the scope of the method by reducing nitro groups in the products to give the corresponding selenium-containing unnatural amino acids.

Supporting Information