Saccharide libraries as potential templates for regio- and chiroselective introduction of two functional groups into [60]fullerene

Tsutomu Ishi-i, Kazuaki Nakashima, Seiji Shinkai, Atsushi Ikeda

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50 Citations (Scopus)

Abstract

This paper reports regio- and chiroselective introduction of two boronic acid groups into [60]fullerene controlled by a saccharide used as a template molecule. The double [4 + 2] cycloadditions between [60]fullerene and 1:2 saccharide-boronic acid complexes 6-9 afforded [60]fullerene-bisadducts 12. Their structures were identified on the basis of 1H and 13C NMR, UV-vis, and CD spectroscopy, mass spectrometry, and chiral HPLC analysis. When 3-O- methyl-D-glucose (4) was used as the template molecule, high regioselectivity was achieved which gave trans-4 isomer 12a as a main isomer in 72.5% yield. The chiro- as well as regioselective preparation of e isomer 12c was attained in 81.4% ee from the 55.7% yield racemic mixture by the reaction using the D- mannitol-3,4-carbonate template (3). When the enantiomers, D-threitol (D-2) and L-threitol (L-2) were used as the templates, cis-3 isomers 12b and ent- 12b with opposite chirality were yielded in 44.2 and 45.2% ee, respectively. On the other hand, 1-O-methyl-α-D-mannopyranoside template (5) featured nonselective cycloaddition.

Original languageEnglish
Pages (from-to)984-990
Number of pages7
JournalJournal of Organic Chemistry
Volume64
Issue number3
DOIs
Publication statusPublished - Feb 5 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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