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Contents Vol 64(11)

Enantioselective Synthesis of Arylglycine Derivatives by Asymmetric Addition of Arylboronic Acids to Imines

Yasunori Yamamoto A B , Yoshinori Takahashi A , Kazunori Kurihara A and Norio Miyaura A
+ Author Affiliations
- Author Affiliations

A Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.

B Corresponding author. Email: yasuyama@eng.hokudai.ac.jp

Australian Journal of Chemistry 64(11) 1447-1453 https://doi.org/10.1071/CH11225
Submitted: 2 June 2011  Accepted: 24 August 2011   Published: 16 November 2011

Abstract

Rhodium-catalyzed enantioselective 1,2-additions of arylboronic acids to N-tosyl furanylimine and lithium 5-methyl-2-furanyltriolborate to N-tosyl arylimines giving aryl(2-furanyl)methanamines were developed for enantioselective synthesis of arylglycines by ozonolysis of the furyl ring. A chiral N-linked C2-symmetric bidentate phosphoramidite (N-Me-BIPAM) achieved high enantioselectivities up to 99 % ee. For the direct synthesis of arylglycines, the asymmetric addition of arylboronic acids to ethyl N-p-methoxyphenyl iminoester was carried out at 80°C in dioxane in the presence of Rh(acac)(C2H4)2/(R,R)-N-Me-BIPAM. The reaction gave optically active arylglycines in up to 99 % ee.


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