Bi(OTf)3-, TfOH-, and TMSOTf-Mediated, One-Pot Epoxide Rearrangement, Addition, and Intramolecular Silyl-Modified Sakurai (ISMS) Cascade toward Dihydropyrans: Comparison of Catalysts and Role of Bi(OTf)3

Authors

R. Frederick Lambert
Robert J. Hinkle
Stephen E. Ammann
et al.
Robert D. Pike, William & MaryFollow

Document Type

Article

Department/Program

Chemistry

Journal Title

The Journal of Organic Chemistry

Pub Date

9-2011

Volume

76

Issue

22

First Page

9269

Abstract

Catalytic quantities of bismuth(III) triflate efficiently initiate the rearrangement of epoxides to aldehydes, which subsequently react with (Z)-δ-hydroxyalkenylsilanes to afford 2,6-disubstituted 3,6-dihydro-2H-pyrans. Isolated yields of desired products using Bi(OTf)3 were compared with yields obtained when the reactions were run with TfOH and TMSOTf in the presence and absence of several additives. These studies, as well as NMR spectroscopic analyses, indicate an initial Lewis acid/base interaction between Bi(OTf)3 and substrates providing TfOH in situ.

Recommended Citation

Lambert, R. Frederick; Hinkle, Robert J.; Ammann, Stephen E.; et al.; and Pike, Robert D., Bi(OTf)3-, TfOH-, and TMSOTf-Mediated, One-Pot Epoxide Rearrangement, Addition, and Intramolecular Silyl-Modified Sakurai (ISMS) Cascade toward Dihydropyrans: Comparison of Catalysts and Role of Bi(OTf)3 (2011). The Journal of Organic Chemistry, 76(22), 9269-9277.
https://doi.org/10.1021/jo201478d

DOI

https://doi.org/10.1021/jo201478d