Facile synthesis of structurally diverse 3,3'-disubstituted 1,1'-binaphthyl-2,2'-diamines in optically pure forms

Taichi Kano; Youhei Tanaka; Kenta Osawa; Taiga Yurino; Keiji Maruoka

doi:10.1021/jo8011368

Facile synthesis of structurally diverse 3,3'-disubstituted 1,1'-binaphthyl-2,2'-diamines in optically pure forms

J Org Chem. 2008 Sep 19;73(18):7387-9. doi: 10.1021/jo8011368. Epub 2008 Aug 15.

Authors

Taichi Kano¹, Youhei Tanaka, Kenta Osawa, Taiga Yurino, Keiji Maruoka

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.

PMID: 18702550
DOI: 10.1021/jo8011368

Abstract

A new synthetic route to 3,3'-dihalo BINAMs based on the direct halogenation of H8-BINAM and subsequent rearomatization to the binaphthyl core has been developed. The combination of this new procedure and Pd-catalyzed coupling reactions enabled us to synthesize various 3,3'-disubstituted BINAMs in only three steps starting from H8-BINAM.

Publication types

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

MeSH terms

Diamines / chemical synthesis*
Diamines / chemistry
Molecular Conformation
Naphthalenes / chemical synthesis*
Naphthalenes / chemistry
Stereoisomerism

Substances

1,1'-binaphthyl-2,2'-diamine
Diamines
Naphthalenes