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Org Lett. 2013 Dec 20;15(24):6178-81. doi: 10.1021/ol4033072. Epub 2013 Nov 26.

Chiral copper(II) complex-catalyzed reactions of partially protected carbohydrates.

Author information

1
Department of Chemistry, Yale University , P.O. Box 208107, New Haven, Connecticut 06520, United States.

Abstract

Catalyst-controlled regioselective functionalization of partially protected saccharide molecules is a highly important yet under-developed area of carbohydrate chemistry. Such reactions allow for the reduction of protecting group manipulation steps required in syntheses involving sugars. Herein, an approach to these processes using enantiopure copper-bis(oxazoline) catalysts to control couplings of electrophiles to various partially protected sugars is reported. In a number of cases, divergent regioselectivity was observed as a function of the enantiomer of catalyst that is used.

PMID:
24274325
DOI:
10.1021/ol4033072
[Indexed for MEDLINE]

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