Chiral Atropisomeric 8,8'-Diiodobinaphthalene for Asymmetric Dearomatizing Spirolactonizations in Hypervalent Iodine Oxidations

Toshifumi Dohi; Hirotaka Sasa; Keitaro Miyazaki; Mihoyo Fujitake; Naoko Takenaga; Yasuyuki Kita

doi:10.1021/acs.joc.7b02037

Chiral Atropisomeric 8,8'-Diiodobinaphthalene for Asymmetric Dearomatizing Spirolactonizations in Hypervalent Iodine Oxidations

J Org Chem. 2017 Nov 17;82(22):11954-11960. doi: 10.1021/acs.joc.7b02037. Epub 2017 Oct 16.

Authors

Toshifumi Dohi¹, Hirotaka Sasa¹, Keitaro Miyazaki¹, Mihoyo Fujitake², Naoko Takenaga³, Yasuyuki Kita⁴

Affiliations

¹ College of Pharmaceutical Sciences, Ritsumeikan University , 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.
² Central Research Laboratories, Osaka University of Pharmaceutical Sciences , 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
³ Department of Chemical Science and Technology, Hosei University , Kajino-cho 3-7-2, Koganei, Tokyo 184-8584, Japan.
⁴ Research Organization of Science and Technology, Ritsumeikan University , 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.

PMID: 28982239
DOI: 10.1021/acs.joc.7b02037

Abstract

A new type of binaphthyl-based chiral iodide functionalized at positions 8 and 8' of the naphthalene rings has been found as a promising structural motif for the asymmetric hypervalent iodine(III) oxidations, specifically, for the dearomatizing spirocyclization of naphthol carboxylic acids showing expectedly better enantioselectivities versus other atropisomeric biaryls, i.e., a conventionally used binaphthalene having the diiodides in the minor groove.

Publication types

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