A General Organocatalytic Enantioselective Nitrocyclopropanation Reaction

Veit Wascholowski; Henriette M. Hansen; Deborah A. Longbottom; Steven V. Ley

doi:10.1055/s-2008-1042944

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Synthesis 2008(8): 1269-1275
DOI: 10.1055/s-2008-1042944

PAPER

A General Organocatalytic Enantioselective Nitrocyclopropanation Reaction

Veit Wascholowski, Henriette M. Hansen, Deborah A. Longbottom, Steven V. Ley*
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK
Fax: +44(1223)336442; e-Mail: svl1000@cam.ac.uk;

Further Information

Publication History

Received 21 December 2007
Publication Date:
18 March 2008 (online)

Abstract
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Abstract

A general organocatalytic enantioselective synthesis of nitrocyclopropanes from bromonitromethane and a variety of cyclic and acyclic enones is described.

Key words

asymmetric catalysis - carbocycles - cyclisation - organocatalysis - nitrocyclopropane - tetrazole

References

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20

The reaction between bromonitromethane (3) and morpholine (4) may lead to the formation of the product 22 (Figure [2] ), which is confirmed by ¹H and ¹³C NMR spectroscopy. MS analysis was unsuccessful.

*Figure 2* Product formed from the reaction of bromonitromethane (3) and morpholine (4)

21

One recrystallisation gives material of ÷99% ee.