Synthesis of trans-1, trans-2, trans-3, and trans-4 bisadducts of C 60 by regio-and stereoselective tether-directed remote functionalization

Sergey Sergeyev, Michael Schär, Paul Seiler, Olena Lukoyanova, Luis Echegoyen, François Diederich

Research output: Contribution to journalArticle

Abstract

The double Bingel reaction of fullerene C60, with bismalonates attached to a Tröger base derived tether afforded trans-1, trans-2, trans-3, and trans-4 bisadducts with excellent regioselectivity. In particular, enantiomerically pure bisadducts with inherently chiral trans-2 or trans-3 addition patterns were prepared starting from enantiomerically pure bismalonates. The absolute configuration of the trans-2 and trans-3 bisadducts was established from their CD spectra. The excellent diastereoselectivity in the double additions to give the trans-2 bisadducts is particularly remarkable given the large distance between the two reacting bonds in opposite hemispheres of the fullerene that is spanned by the tether. Now, all inherently chiral double addition patterns are readily available by tether-directed functionalization using appropriate chiral, non-racemic spacers.

Original languageEnglish (US)
Pages (from-to)2284-2294
Number of pages11
JournalChemistry - A European Journal
Volume11
Issue number8
DOIs
StatePublished - Apr 8 2005
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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