Selective Synthesis of Partially Protected d-Talopyranosides and d-Gulopyranosides via Catalytic Asymmetric Dihydroxylation: Multiplier Effects of Substrate Control and Catalyst Control

Yoichi Namito; Kyosuke Michigami; Takaaki Nagahashi; Ryosuke Matsubara; Masahiko Hayashi

doi:10.1021/acs.orglett.6b03000

Selective Synthesis of Partially Protected d-Talopyranosides and d-Gulopyranosides via Catalytic Asymmetric Dihydroxylation: Multiplier Effects of Substrate Control and Catalyst Control

Org Lett. 2016 Dec 2;18(23):6058-6061. doi: 10.1021/acs.orglett.6b03000. Epub 2016 Nov 11.

Authors

Yoichi Namito¹, Kyosuke Michigami¹, Takaaki Nagahashi¹, Ryosuke Matsubara¹, Masahiko Hayashi¹

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kobe University , Kobe 657-8501, Japan.

PMID: 27934352
DOI: 10.1021/acs.orglett.6b03000

Abstract

Highly selective syntheses of d-talopyranosides and d-gulopyranosides have been achieved by utilizing the multiplier effects of substrate control and catalyst control. Through the combination of an O-benzoyl-protected substrate and the AD-mix-β system, the d-talopyranoside was obtained in a ratio of 96:4. In contrast, the d-gulopyranoside was obtained in a ratio of 3:97 through the use of an O-tert-butyldimethylsilyl-protected substrate and AD-mix-α.

Publication types

Research Support, Non-U.S. Gov't