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High Enantioselective Organocatalytic Asymmetric Direct Aldol Reactions of Aldehydes with Long-Chain Aliphatic Ketones

高强, Jun Li, LI Can

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Abstract

Asymmetric organocatalysis have been developed explosively, since the pioneering work on\nproline-catalyzed asymmetric direct Aldol reaction reported by List, Barbas and coworkers[1].\nNumerous organocatalysts have been designed and the stereochemistry of the Aldol reactions has been\nsignificantly improved. However, organocatalytic direct aldol reactions of aldehydes with long-chain\nacyclic aliphatic ketones have been less investigated[2][3]. Herein, we report diamine catalytic aldol\nreaction of acyclic aliphatic ketones with aromatic aldehydes, providing high enantioselectivities. In\nneat condition, these aldol reactions afforded Aldol products with 80–96% ee.

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Asymmetric organocatalysis have been developed explosively, since the pioneering work on\nproline-catalyzed asymmetric direct Aldol reaction reported by List, Barbas and coworkers[1].\nNumerous organocatalysts have been designed and the stereochemistry of the Aldol reactions has been\nsignificantly improved. However, organocatalytic direct aldol reactions of aldehydes with long-chain\nacyclic aliphatic ketones have been less investigated[2][3]. Herein, we report diamine catalytic aldol\nreaction of acyclic aliphatic ketones with aromatic aldehydes, providing high enantioselectivities. In\nneat condition, these aldol reactions afforded Aldol products with 80–96% ee.

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Available abstract

Asymmetric organocatalysis have been developed explosively, since the pioneering work on\nproline-catalyzed asymmetric direct Aldol reaction reported by List, Barbas and coworkers[1].\nNumerous organocatalysts have been designed and the stereochemistry of the Aldol reactions has been\nsignificantly improved. However, organocatalytic direct aldol reactions of aldehydes with long-chain\nacyclic aliphatic ketones have been less investigated[2][3]. Herein, we report diamine catalytic aldol\nreaction of acyclic aliphatic ketones with aromatic aldehydes, providing high enantioselectivities. In\nneat condition, these aldol reactions afforded Aldol products with 80–96% ee.

Key concepts: Aldol reaction, Enantioselective synthesis, Organocatalysis, Chemistry, Organic chemistry, Catalysis, Diamine

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