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Letter

Asymmetric Mannich Reactions with in Situ Generation of Carbamate-Protected Imines by an Organic Catalyst

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Jun Song, Hui-Wen Shih, and Li Deng*

Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110

Org. Lett., 2007, 9 (4), pp 603–606

DOI: 10.1021/ol062837q

Publication Date (Web): January 27, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, deng@brandeis.edu

Abstract

The instability of carbamate-protected alkyl imines has greatly hampered the development of catalytic asymmetric Mannich reactions suitable for the synthesis of optically active carbamate-protected chiral alkyl amines. A highly enantioselective Mannich reaction with in situ generation of carbamate-protected imines from stable α-amido sulfones catalyzed by an organic catalyst was developed. This reaction provides a concise and highly enantioselective route converting aromatic and aliphatic aldehydes into optically active aryl and alkyl β-amino acids.

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Published In Issue February 15, 2007
Received November 21, 2006

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Letter

Asymmetric Mannich Reactions with in Situ Generation of Carbamate-Protected Imines by an Organic Catalyst

Abstract

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History

Recommend & Share

Related Content

The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids: Enantioselective Synthesis of β-Amino Acids The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids: Enantioselective Synthesis of β-Amino Acids

Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives: Enantioselective Synthesis of β-Aryl-β-Amino Acids

Control of Diastereoselectivity in Tandem Asymmetric Reactions Generating Nonadjacent Stereocenters with Bifunctional Catalysis by Cinchona Alkaloids

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