Synlett 2014; 25(5): 603-607
DOI: 10.1055/s-0033-1340467
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© Georg Thieme Verlag Stuttgart · New York

Efficient and Stereoselective Nitration of Olefins with AgNO2 and TEMPO

Soham Maity
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India   Email: dmaiti@chem.iitb.ac.in
,
Togati Naveen
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India   Email: dmaiti@chem.iitb.ac.in
,
Upendra Sharma
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India   Email: dmaiti@chem.iitb.ac.in
,
Debabrata Maiti*
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India   Email: dmaiti@chem.iitb.ac.in
› Author Affiliations
Further Information

Publication History

Received: 08 October 2013

Accepted: 21 November 2013

Publication Date:
13 January 2014 (online)

Abstract

Synthetic utility of nitroolefins in fundamental organic synthesis has inspired us to develop a method to access nitroolefins stereoselectively starting from olefins. Silver nitrite along with catalytic TEMPO was found to be the reagent combination of choice. The method enjoys a broad scope and functional-group tolerance while nitroolefins are obtained in high yields with excellent E-selectivity.

 
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