Issue 32, 2017

Site-selective benzoin-type cyclization of unsymmetrical dialdoses catalyzed by N-heterocyclic carbenes for divergent cyclitol synthesis

Abstract

A highly site-selective N-heterocyclic carbene (NHC)-catalyzed benzoin-type cyclization of unsymmetrical dialdoses is developed to enable a divergent cyclitol synthesis. The choice of chiral NHCs and protecting groups affects the site-selectivity. The resulting inososes are converted into epi-, muco- and myo-inositols, and their chiral protected derivatives are formed in good yields.

Graphical abstract: Site-selective benzoin-type cyclization of unsymmetrical dialdoses catalyzed by N-heterocyclic carbenes for divergent cyclitol synthesis

Supplementary files

Article information

Article type
Communication
Submitted
14 Feb 2017
Accepted
29 Mar 2017
First published
29 Mar 2017

Chem. Commun., 2017,53, 4469-4472

Site-selective benzoin-type cyclization of unsymmetrical dialdoses catalyzed by N-heterocyclic carbenes for divergent cyclitol synthesis

B. Kang, Y. Wang, S. Kuwano, Y. Yamaoka, K. Takasu and K. Yamada, Chem. Commun., 2017, 53, 4469 DOI: 10.1039/C7CC01191A

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