One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids

Deiana, Luca, Zhao, Gui-Ling, Dziedzic, Pawel, Rios, Ramon, Vesely, Jan, Ekström, Jesper and Córdova, Armando (2010) One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids. Tetrahedron Letters, 51 (2), 234-237. (doi:10.1016/j.tetlet.2009.10.130).

Abstract

A highly enantioselective catalytic route to carbamate- and benzoate-protected β-amino aldehydes and β-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and α-amido sulfones gives the corresponding β-amino compounds with up to 95:5 dr and 97–>99% ee.

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Contributors

Author: Ramon Rios

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