A mild and general method for the synthesis of 5-substituted and 5,5-disubstituted fulleroprolines

Authors

Rajeswari Thayumanavan, University of WollongongFollow
Bill C. Hawkins, University of Wollongong
Paul A. Keller, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow
Graham E Ball, University of New South Wales

RIS ID

25500

Publication Details

Thayumanavan, R., Hawkins, B. C., Keller, P. A., Pyne, S. G. and Ball, G. (2008). A mild and general method for the synthesis of 5-substituted and 5,5-disubstituted fulleroprolines. Organic Letters, 10 (6), 1315-1317.

Abstract

The reductive ring-opening of fullerenyldihydropyrrole yields ethyl N-benzhydryl fullerenyl[60]glycinate, which is deprotected to give ethyl fullerenylglycinate. The free amine is able to react with a variety of aldehydes and ketones in a Mannich-type process to produce 5-substituted and 5,5-disubstituted fulleroprolines and represents a versatile and general strategy to this class of compounds.