Point-to-Point Ultra-Remote Asymmetric Control with Flexible Linker

Tsuneomi Kawasaki; Yasuyuki Ishikawa; Yoshihiro Minato; Takashi Otsuka; Shigeru Yonekubo; Itaru Sato; Takanori Shibata; Arimasa Matsumoto; Kenso Soai

doi:10.1002/chem.201605076

Point-to-Point Ultra-Remote Asymmetric Control with Flexible Linker

Chemistry. 2017 Jan 5;23(2):282-285. doi: 10.1002/chem.201605076. Epub 2016 Nov 23.

Authors

Tsuneomi Kawasaki^{1

2

3}, Yasuyuki Ishikawa¹, Yoshihiro Minato¹, Takashi Otsuka¹, Shigeru Yonekubo¹, Itaru Sato^{1

4}, Takanori Shibata^{1

5}, Arimasa Matsumoto^{1

2}, Kenso Soai^{1

2}

Affiliations

¹ Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan.
² Research Center for Chirality, Research Institute for Science and Technology (RIST), Tokyo University of Science, Japan.
³ Department of Materials Science and Engineering, University of Fukui, Bunkyo, Fukui, 910-8507, Japan.
⁴ Graduate School of Science and Engineering, Ibaraki University, Bunkyo, Ibaraki, 310-8512, Japan.
⁵ Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo, 169-8555, Japan.

PMID: 27801951
DOI: 10.1002/chem.201605076

Abstract

An ultra-remote intramolecular (point-to-point) asymmetric control through 38 bonds (1,39-asymmetric induction) has been achieved by using the principle of direct supramolecular orientation of catalytic and reactive moieties in asymmetric autocatalysis. We found the highly stereoselective diisopropylzinc addition reaction using designed molecules possessing pyrimidine sites at each terminal of a conformationally flexible simple methylene chain.

Keywords: 5-pyrimidyl alkanol; asymmetric amplification; intramolecular stereocontrol; remote asymmetric induction; stereoselective reaction.

Publication types

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