Transition State Study on the S-Proline-catalyzed Direct Aldol Reaction between Acetone and 2,2-Dimethyl-propionaldehyde

Acta Chimica Sinica ›› 2005, Vol. 63 ›› Issue (8): 677-680. Previous Articles Next Articles

Original Articles

S-脯氨酸催化丙酮与2,2-二甲基丙醛不对称直接羟醛缩合反应过渡态的理论研究

樊建芬*，吴丽芬

(苏州大学化学化工学院江苏省有机合成重点实验室苏州 215006)

投稿日期:2004-09-14 修回日期:2004-12-28 发布日期:2010-12-10
通讯作者: 樊建芬

Transition State Study on the S-Proline-catalyzed Direct Aldol Reaction between Acetone and 2,2-Dimethyl-propionaldehyde

FAN Jian-Fen*, WU Li-Fen

(Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215006)

Received:2004-09-14 Revised:2004-12-28 Published:2010-12-10
Contact: FAN Jian-Fen

Abstract

HF and DFT calculations were employed to study the four stereoisomeric transition states in the stereo-controlling step of the direct aldol reaction between acetone and 2,2-dimethyl-propionaldehyde catalyzed by S-proline. The solvent effect of DMSO was involved. The calculation results revealed the enantioselectivity of the reaction.

Key words: B3LYP, HF, asymmetric catalytic direct aldol reaction, S-proline, acetone, 2,2-dimethyl-propionaldehyde, solvent

Cite this article

FAN Jian-Fen*, WU Li-Fen. Transition State Study on the S-Proline-catalyzed Direct Aldol Reaction between Acetone and 2,2-Dimethyl-propionaldehyde[J]. Acta Chimica Sinica, 2005, 63(8): 677-680.

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S-脯氨酸催化丙酮与2,2-二甲基丙醛不对称直接羟醛缩合反应过渡态的理论研究

Transition State Study on the S-Proline-catalyzed Direct Aldol Reaction between Acetone and 2,2-Dimethyl-propionaldehyde

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