Mannich-type Reaction of Methylene Active Compounds with a Chiral Sulfinimine of Trifluoropyruvate: New Highly Stereoselective Synthesis of (S)-α-Trifluoromethyl-Aspartic Acid

Francesco Lazzaro; Arnaud Gissot; Marcello Crucianelli; Francesco D. Angelis; Luca Bruche; Matteo Zanda

doi:10.2174/1570178053765348

ISSN: 1570-1786
E-ISSN: 1875-6255

Mannich-type Reaction of Methylene Active Compounds with a Chiral Sulfinimine of Trifluoropyruvate: New Highly Stereoselective Synthesis of (S)-α-Trifluoromethyl-Aspartic Acid
Authors: Francesco Lazzaro¹, Arnaud Gissot², Marcello Crucianelli³, Francesco D. Angelis⁴, Luca Bruche⁵ and Matteo Zanda⁶
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¹ Dipartimento di Chimica, Ingegneria Chimica e Materiali, Universita di L'Aquila, via Vetoio, I- 67010 Coppito, Italy. ² Dipartimento di Chimica, Ingegneria Chimica e Materiali, Universita di L'Aquila, via Vetoio, I- 67010 Coppito, Italy. ³ Dipartimento di Chimica, Ingegneria Chimica e Materiali, Universita di L'Aquila, via Vetoio, I- 67010 Coppito, Italy. ⁴ Dipartimento di Chimica, Ingegneria Chimica e Materiali, Universita di L'Aquila, via Vetoio, I- 67010 Coppito, Italy. ⁵ Dipartimento di Chimica, Ingegneria Chimica e Materiali, Universita di L'Aquila, via Vetoio, I- 67010 Coppito, Italy. ⁶ Dipartimento di Chimica, Ingegneria Chimica e Materiali, Universita di L'Aquila, via Vetoio, I- 67010 Coppito, Italy.
Source: Letters in Organic Chemistry, Volume 2, Issue 3, May 2005, p. 235 - 237
DOI: https://doi.org/10.2174/1570178053765348
- Available online: 01 May 2005

Abstract

A strongly improved, highly stereoselective synthesis of (S)-α-trifluoromethyl aspartic acid via addition of lithium malonate to a chiral sulfinimine of trifluoropyruvate is presented.

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2005-05-01

2025-09-07

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Article Type: Review Article

Keyword(s): fluorine; mannich-reaction; stereoselective synthesis; sulfinimines; trifluoromethyl amino acids

Mannich-type Reaction of Methylene Active Compounds with a Chiral Sulfinimine of Trifluoropyruvate: New Highly Stereoselective Synthesis of (S)-α-Trifluoromethyl-Aspartic Acid

Abstract

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