Lithio Tris(methylthio)methane as Hydroxy/Thio/Aminocarbonyl Anion Equivalent: Asymmetric Synthesis of α-Amino Acid Esters, Thioesters, Amides, and Peptides

Kesavulu, G and Balachandra, B and Prasad, KR (2023) Lithio Tris(methylthio)methane as Hydroxy/Thio/Aminocarbonyl Anion Equivalent: Asymmetric Synthesis of α-Amino Acid Esters, Thioesters, Amides, and Peptides. In: Organic Letters .

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Abstract

The use of lithio tris(methylthio)methane as a hydroxy/thio/amino carbonyl anion equivalent in the synthesis of α-amino acids is reported. Addition of the reagent to nonracemic sulfinimines furnished the α-sulfinamido trithioformates in excellent diastereoselectivity. Unmasking the trithioformates to diverse functionalities, such as α-amino acid thioesters, esters, anilides, amides, and di/tri peptides, without epimerization of chiral centers was accomplished.

Item Type:	Journal Article
Publication:	Organic Letters
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to the American Chemical Society.
Keywords:	amide; amino acid; anion; ester; methane; peptide; sulfur derivative, chemistry; stereoisomerism, Amides; Amino Acids; Anions; Esters; Methane; Peptides; Stereoisomerism; Sulfur Compounds
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	31 Jul 2023 11:31
Last Modified:	31 Jul 2023 11:31
URI:	https://eprints.iisc.ac.in/id/eprint/82760

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