Preparation of chiral bromomethylenecyclopropane and its use in Suzuki-Miyaura coupling: synthesis of the arylmethyl-(Z)-cyclopropane structure core

Makoto Tanabe; Mizuki Watanabe; Naoyuki Hoshiya; Akira Mizuno; Hayato Fukuda; Mitsuhiro Arisawa; Satoshi Shuto

doi:10.1021/jo401675z

Preparation of chiral bromomethylenecyclopropane and its use in Suzuki-Miyaura coupling: synthesis of the arylmethyl-(Z)-cyclopropane structure core

J Org Chem. 2013 Dec 6;78(23):11714-20. doi: 10.1021/jo401675z. Epub 2013 Nov 20.

Authors

Makoto Tanabe¹, Mizuki Watanabe, Naoyuki Hoshiya, Akira Mizuno, Hayato Fukuda, Mitsuhiro Arisawa, Satoshi Shuto

Affiliation

¹ Faculty of Pharmaceutical Sciences and ‡Center for Research and Education on Drug Development, Hokkaido University , Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

PMID: 24206361
DOI: 10.1021/jo401675z

Abstract

A preparative method for an optically active bromomethylenecyclopropane unit and its practical conversion to (Z)-cyclopropane-containing chiral compounds via Suzuki-Miyaura coupling were established.

Publication types

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

MeSH terms

Cyclopropanes / chemical synthesis*
Cyclopropanes / chemistry
Hydrocarbons, Brominated / chemical synthesis*
Hydrocarbons, Brominated / chemistry
Molecular Structure
Stereoisomerism

Substances

Cyclopropanes
Hydrocarbons, Brominated