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Synthesis 2005(4): 583-587  
DOI: 10.1055/s-2005-861788
PAPER
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by (1R,2R)-10-(Dialkylamino)isoborneols

Yoshiyuki Hari, Toyohiko Aoyama*
Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan
Fax: +81(52)8363439; e-Mail: aoyama@phar.nagoya-cu.ac.jp;
Further Information

Publication History

Received 25 October 2004
Publication Date:
18 January 2005 (online)

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Abstract

(1R,2R)-10-Dialkylaminoisoborneols, γ-amino alcohol-type ligands, were synthesized from (+)-ketopinic acid. Their catalytic ability as a chiral ligand for enantioselective addition of diethylzinc to aldehydes was evaluated. Among them, the ligand with a 9-azabicyclo[3.3.1]nonan-9-yl group as an amino moiety was the most effective and showed good enantioselectivity towards various aldehydes.

Key words

aldehydes - amino alcohols - diethylzinc - enantioselective addition - enantioselectivity

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