Synthesis 2007(16): 2461-2470  
DOI: 10.1055/s-2007-983787
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Applications of 3-[6-(Hydroxymethyl)pyridin-2-yl]-1,1′-bi-2-naphthols or 3,3′-Bis[6-(hydroxymethyl)pyridin-2-yl]-1,1′-bi-2-naphthols

Li Ma, Rin-Zhe Jin, Guang-Hua Lü, Zhen Bian, Meng-Xian Ding, Lian-Xun Gao*
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022, P. R. of China
Fax: +86(431)85697831; e-Mail: [email protected];
Further Information

Publication History

Received 9 January 2007
Publication Date:
12 July 2007 (online)

Abstract

A series of new 1,1′-bi-2-naphthol (BINOL) derived ligands, 3-[6-(hydroxymethyl)pyridin-2-yl]-BINOLs or 3,3′-bis[6-(hydroxymethyl)pyridin-2-yl]-BINOLs, bearing one or two chiral pyridinylmethanols attached to a binaphthyl skeleton, have been synthesized using the Suzuki cross-coupling reaction. The resulting compounds have been used as ligands in the enantioselective addition of diethylzinc to aldehydes; the products were obtained with up to 96% ee.

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7

The product with one MOM removed was determined by 1H NMR.