Display options
Cite
Mandai H, Yasuhara H, Fujii K, et al. Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1'-Binaphthyl Unit: Importance of the Hydroxy Groups. J Org Chem. 2017;82(13):6846-6856doi: 10.1021/acs.joc.7b00992.
Mandai, H., Yasuhara, H., Fujii, K., Shimomura, Y., Mitsudo, K., & Suga, S. (2017). Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1'-Binaphthyl Unit: Importance of the Hydroxy Groups. The Journal of organic chemistry, 82(13), 6846-6856. https://doi.org/10.1021/acs.joc.7b00992
Mandai, Hiroki, et al. "Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1'-Binaphthyl Unit: Importance of the Hydroxy Groups." The Journal of organic chemistry vol. 82,13 (2017): 6846-6856. doi: https://doi.org/10.1021/acs.joc.7b00992
Mandai H, Yasuhara H, Fujii K, Shimomura Y, Mitsudo K, Suga S. Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1'-Binaphthyl Unit: Importance of the Hydroxy Groups. J Org Chem. 2017 Jul 07;82(13):6846-6856. doi: 10.1021/acs.joc.7b00992. Epub 2017 Jun 14. PMID: 28561589.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2017 Jul 07;82(13):6846-6856. doi: 10.1021/acs.joc.7b00992. Epub 2017 Jun 14.

Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1'-Binaphthyl Unit: Importance of the Hydroxy Groups.

The Journal of organic chemistry

Hiroki Mandai, Hiroshi Yasuhara, Kazuki Fujii, Yukihito Shimomura, Koichi Mitsudo, Seiji Suga

Affiliations

  1. Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.

PMID: 28561589 DOI: 10.1021/acs.joc.7b00992

Abstract

We developed an acylative desymmetrization of meso-1,2-diols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1h with tert-alcohol substituents. The reaction proceeds with a wide range of acyclic meso-1,2-diols and six-membered-ring meso-1,2-diols to provide a monoacylate selectively with a high enantiomeric ratio (er). Only 0.1 mol % of the catalyst facilitated the reaction within a short reaction time (3 h) to afford enantio-enriched monoacylated products in moderate to good yield. Several control experiments revealed that the tert-alcohol units of catalyst 1h play a significant role in achieving high catalytic activity, chemoselectivity of monoacylation, and enantioselectivity.

Publication Types