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Sulfinimines of trifluoropyruvate: Novel intermediates for chiral non racemic α-trifluoromethyl α-amino acids

✍ Scribed by Pierfrancesco Bravo; Marcello Crucianelli; Barbara Vergani; Matteo Zanda

Book ID
104259986
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
308 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new and prepamtively useful method for the synthesis of non racemic ct.trifluoromethyl ('grin) or-amino acids (AAs) is presented. Kcy-lmilding blocks are the sulfinirqines (S)-la,b, prepared via Sta, u41ng¢lreaction from triflu~c (mttt's and the chiral N-sulfinyl iminophosphorane (S)-5, which were reacted with bemzyl and alk~um halides. The rtmflting N-sulfinyl a-Tfin (z-amino esters 6a,b and 6¢-1, respectively, were peeduced with opposite slxmmseleclivity. The stereoconlrol with alkyl Grignard rease~ was lm~remively high~ with increasing_ steric bull Some of the adducts 6 were transformed into cL-Tfm-phcnyialan~ (R)-8 (with r~gcal~afion and r~yoling the chiral auxiliary), (z-Tfm-l~fin¢ (5")-11¢, ~-Tfin-butyrin¢ (5~-11f and ~-Tfm-alan~ (~)-11g in two steps in one-pot.

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ChemInform Abstract: Highly Diastereoselective Synthesis of Quaternary α-Trifluoromethyl α-Amino Acids from Chiral Imines of Trifluoropyruvate.
✍ Qiao-Qiao Min; Chun-Yang He; Haibing Zhou; Xingang Zhang 📂 Article 📅 2011 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

## Abstract An efficient highly diastereoselective synthesis of quaternary α‐trifluoromethyl amino acids (III) and (V) is developed via allylation of enantiopure imines of trifluoropyruvate (I).