Alkyl 2-(2-benzothiazolylsulfinyl)acetates as useful synthetic reagents for alkyl 4-hydroxyalk-2-enoates by sulfinyl-Knoevenagel reaction

Autor:	Zhen-Jun Du, Rikiya Omatsu, Toshihiro Kawatani, Junzo Nokami, Kazuhide Kataoka
Rok vydání:	2012
Předmět:	chemistry.chemical_classification Organic Chemistry Enantioselective synthesis Biochemistry Kinetic resolution chemistry.chemical_compound chemistry Reagent Drug Discovery Mislow–Evans rearrangement Organic chemistry Organic synthesis Knoevenagel condensation Alkyl Isopropyl
Zdroj:	Tetrahedron. 68:2471-2480
ISSN:	0040-4020
DOI:	10.1016/j.tet.2012.01.057
Popis:	Isopropyl, ethyl, and methyl 2-(2-benzothiazolylsulfinyl)acetates have been found to be useful synthetic reagents for sulfinyl-Knoevenagel reaction with various aldehydes to give directly the corresponding 4-hydroxyalk-2-enoates [R′CH(OH)CH CHCO2R], which are ubiquitous structures in biologically active natural products and useful building blocks for organic synthesis of chiral compounds. From the optically pure (R)-2-(2-benzothiazolylsulfinyl)acetates (>99% ee) prepared by the enzymatic kinetic resolution of (±)-2-(2-benzothiazolylsulfinyl)acetates, optically active 4-hydroxyalk-2-enoates (up to 91% ee) have been obtained in good yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::68e8e7cbf04f50ab4e582ac6f9ade9b8 https://doi.org/10.1016/j.tet.2012.01.057 Zobrazit plný text záznamu Full Text from ScienceDirect