Display options
Cite
Tay JH, Arguelles AJ, Nagorny P. Direct Interconversion of BINOL and H8-BINOL-Based Chiral Brønsted Acids Using Single-Step Red/Ox Manipulations. Org Lett. 2015;17(15):3774-7doi: 10.1021/acs.orglett.5b01754.
Tay, J. H., Arguelles, A. J., & Nagorny, P. (2015). Direct Interconversion of BINOL and H8-BINOL-Based Chiral Brønsted Acids Using Single-Step Red/Ox Manipulations. Organic letters, 17(15), 3774-7. https://doi.org/10.1021/acs.orglett.5b01754
Tay, Jia-Hui, et al. "Direct Interconversion of BINOL and H8-BINOL-Based Chiral Brønsted Acids Using Single-Step Red/Ox Manipulations." Organic letters vol. 17,15 (2015): 3774-7. doi: https://doi.org/10.1021/acs.orglett.5b01754
Tay JH, Arguelles AJ, Nagorny P. Direct Interconversion of BINOL and H8-BINOL-Based Chiral Brønsted Acids Using Single-Step Red/Ox Manipulations. Org Lett. 2015 Aug 07;17(15):3774-7. doi: 10.1021/acs.orglett.5b01754. Epub 2015 Jul 21. PMID: 26196463.
Copy Download .nbib Format: NLM
Share it on

Org Lett. 2015 Aug 07;17(15):3774-7. doi: 10.1021/acs.orglett.5b01754. Epub 2015 Jul 21.

Direct Interconversion of BINOL and H8-BINOL-Based Chiral Brønsted Acids Using Single-Step Red/Ox Manipulations.

Organic letters

Jia-Hui Tay, Alonso J Arguelles, Pavel Nagorny

Affiliations

  1. Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.

PMID: 26196463 DOI: 10.1021/acs.orglett.5b01754

Abstract

A direct single-step hydrogenation of BINOL-based chiral phosphoric acids, N-triflyl phosphoramides, and disulfonimides to the corresponding H8-BINOL Brønsted acids in excellent yields and chemoselectivities is described. In addition, the conditions for the single-step oxidation of H8-BINOL-based Brønsted acids into the corresponding BINOL-based acids have been identified and employed to accomplish these interconversions in 41-81% yield.

Publication Types