Silanediols: a new class of hydrogen bond donor catalysts

Andrew G Schafer; Joshua M Wieting; Anita E Mattson

doi:10.1021/ol2021115

Silanediols: a new class of hydrogen bond donor catalysts

Org Lett. 2011 Oct 7;13(19):5228-31. doi: 10.1021/ol2021115. Epub 2011 Sep 6.

Authors

Andrew G Schafer¹, Joshua M Wieting, Anita E Mattson

Affiliation

¹ Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.

PMID: 21894881
DOI: 10.1021/ol2021115

Abstract

Silanediols are introduced as a new class of hydrogen bond donor catalysts for the activation of nitroalkenes toward nucleophilic attack. Excellent yields of product are obtained for the conjugate addition of indole to β-nitrostyrene catalyzed with a stable, storable dinaphthyl-derived silanediol. The preparation and structural characterization of a C(2)-symmetric chiral silanediol is also reported along with its ability to catalyze the conjugate addition reaction.