论文信息 - Direct asymmetric aldol reactions catalyzed by (4R)-4-(beta-Naphthalenyl)methoxy-(S)-proline.

Direct asymmetric aldol reactions catalyzed by (4R)-4-(beta-Naphthalenyl)methoxy-(S)-proline.

A novel proline derivative, (4R)-4-(beta-Naphthalenyl)methoxy-(S)-proline, was conveniently prepared from the naturally occurring (4S)-hydroxy-(S)-proline; 5 mol % of this compound efficiently catalyzes the asymmetric aldol reactions of various benzaldehydes with acetone in excess of acetone as the solvent, giving the aldol adducts in good yields with ee up to 89.8%.

[1] B List,et al. Proline-catalyzed asymmetric aldol reactions between ketones and alpha-unsubstituted aldehydes. , 2001, Organic letters.

[2] D. MacMillan,et al. The first direct and enantioselective cross-aldol reaction of aldehydes. , 2002, Journal of the American Chemical Society.

[3] C. Barbas,et al. Amino acid catalyzed direct asymmetric aldol reactions: a bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions. , 2001, Journal of the American Chemical Society.

[4] B. List. Proline-catalyzed asymmetric reactions , 2002 .

[5] B. Neustadt,et al. Synthesis and pharmacological activity of angiotensin converting enzyme inhibitors: N-(mercaptoacyl)-4-substituted-(S)-prolines. , 1988, Journal of medicinal chemistry.

[6] Richard A. Lerner,et al. Proline-Catalyzed Direct Asymmetric Aldol Reactions , 2000 .

[7] B. List,et al. Catalytic Asymmetric Synthesis of anti-1,2-Diols , 2000 .

[8] M. L. Peterson,et al. Synthesis and biological evaluation of 4-purinylpyrrolidine nucleosides. , 1991, Journal of medicinal chemistry.

[9] Amino acids and peptides as asymmetric organocatalysts , 2002 .