Synthesis of Cage-Shaped Aluminum Aryloxides: Efficient Lewis Acid Catalyst for Stereoselective Glycosylation Driven by Flexible Shift of Four- to Five-Coordination

Daiki Tanaka; Yuichiro Kadonaga; Yoshiyuki Manabe; Koichi Fukase; Shota Sasaya; Hikaru Maruyama; Sota Nishimura; Mayu Yanagihara; Akihito Konishi; Makoto Yasuda

doi:10.1021/jacs.9b08875

Synthesis of Cage-Shaped Aluminum Aryloxides: Efficient Lewis Acid Catalyst for Stereoselective Glycosylation Driven by Flexible Shift of Four- to Five-Coordination

J Am Chem Soc. 2019 Nov 6;141(44):17466-17471. doi: 10.1021/jacs.9b08875. Epub 2019 Oct 3.

Authors

Daiki Tanaka¹, Yuichiro Kadonaga^{2

3}, Yoshiyuki Manabe^{3

4}, Koichi Fukase^{3

4}, Shota Sasaya¹, Hikaru Maruyama¹, Sota Nishimura¹, Mayu Yanagihara³, Akihito Konishi^{1

5}, Makoto Yasuda¹

Affiliations

¹ Department of Applied Chemistry, Graduate School of Engineering , Osaka University , 2-1 Yamadaoka , Suita , Osaka 565-0871 , Japan.
² Division of Science, Institute for Radiation Sciences , Osaka University , 1-1 Machikaneyama , Toyonaka , Osaka 560-0043 , Japan.
³ Department of Chemistry, Graduate School of Science , Osaka University , 1-1 Machikaneyama , Toyonaka , Osaka 560-0043 , Japan.
⁴ Core for Medicine and Science Collaborative Research and Education, Project Research Center for Fundamental Science , Osaka University , 1-1 Machikaneyama , Toyonaka , Osaka 560-0043 , Japan.
⁵ Center for Atomic and Molecular Technologies, Graduate School of Engineering , Osaka University , 2-1 Yamadaoka , Suita , Osaka 565-0871 , Japan.

PMID: 31573807
DOI: 10.1021/jacs.9b08875

Abstract

Monomeric cage-shaped aluminum aryl oxides 1Al were synthesized using tripodal triphenolic ligands. The Lewis acidity and catalytic activity of the obtained 1Al·py were investigated. The Lewis acidity of 1Al·py originates from the flexible change in the coordination number of the aluminum center, allowing the catalytic O-glycosylation to occur with a high efficiency and an unusual stereoselectivity.

Publication types

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