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Two effective procedures for the synthesis of trichloromethyl ketones, useful precursors of chiral α-amino and α-hydroxy acids

✍ Scribed by E.J. Corey; John O. Link; Yang Shao

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
305 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

Trichloroacetic acid can be converted to trichloromethyl ketones in good yield by two practical new procedures, one involving the catalyzed reaction of trichloroacetic acid with aldehydes at 23 eY: followed by oxidation and the other utilizing the coupling of organozinc intermediates with m'chloroacetyl chloride.

Chiral a-trichloro-and tribmmomethyl carbinols have assumed a new importance because they can be prepared in high enantiomeric purity by oxazaborolidine catalyzed (CBS) reduction of the corresponding ketone& and can be easily converted to enantiomerically pure a-amino acids and a-hydroxy acids.3 The utility of trichloromethyl carbinols and the lack of satisfactory procedures for the production of their precursor ketones prompted us to investigate improved methods of trichloromethyl ketone synthesis. Herein we describe two

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✍ Y Le Merrer; C Gravier-Pelletier; J Dumas; J.C Depezay 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 273 KB

&mm6fy : The four possible stereoisomers of a$dihydroxyaldehydes, useful building blocks for the synthesis of fatty acids metabolites, are synthesized via epoxy-tetrols derived from D-isoascorbic and L-ascorbic acids. The general method we develop allows the synthesis of chiral a-hydroxyaldehydes as