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2006•Advanced Synthesis & CatalysisRequires access

4,4′‐Disubstituted L ‐Prolines as Highly Enantioselective Catalysts for Direct Aldol Reactions

Liuqun Gu, Menglong Yu, Xiaoyu Wu, Yazhu Zhang, Gang Zhao

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Abstract

Abstract A new series of 4,4′‐disubstituted prolines (1a–h) has been developed and tested as organocatalysts in the direct catalytic asymmetric aldol reaction of several aliphatic ketones with aldehydes. Catalyst 1g affords the best enantioselectivities for this transformation. The reaction was carried out in DMF using a catalyst loading of 10 mol % at −10 °C to give the aldol products in up to 97 % ee for acetone. In the cases of cyclohexanone and cyclopentanone, the corresponding anti‐products were obtained in 94 % ee.

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What this paper is about

Abstract A new series of 4,4′‐disubstituted prolines (1a–h) has been developed and tested as organocatalysts in the direct catalytic asymmetric aldol reaction of several aliphatic ketones with aldehydes. Catalyst 1g affords the best enantioselectivities for this transformation. The reaction was carried out in DMF using a catalyst loading of 10 mol % at −10 °C to give the aldol products in up to 97 % ee for acetone. In the cases of cyclohexanone and cyclopentanone, the corresponding anti‐products were obtained in 94 % ee.

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Available abstract

Abstract A new series of 4,4′‐disubstituted prolines (1a–h) has been developed and tested as organocatalysts in the direct catalytic asymmetric aldol reaction of several aliphatic ketones with aldehydes. Catalyst 1g affords the best enantioselectivities for this transformation. The reaction was carried out in DMF using a catalyst loading of 10 mol % at −10 °C to give the aldol products in up to 97 % ee for acetone. In the cases of cyclohexanone and cyclopentanone, the corresponding anti‐products were obtained in 94 % ee.

Key concepts: Aldol reaction, Chemistry, Cyclohexanone, Cyclopentanone, Enantioselective synthesis, Catalysis, Acetone, Organic chemistry

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