Title

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

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.

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Link to publisher version (DOI)

http://dx.doi.org/10.1021/ol8002157