ChemInform Abstract: The Use of Chiral Auxiliaries Prepared from (-)-β-Pinene in Stereoselective Reduction of β-Ketobutyrates

Autor:	Paulo R. R. Costa, Karla G. Alencar, Ubiracir F.L. Filho, Mário L. A. A. Vasconcellos
Rok vydání:	2010
Předmět:	Pinene chemistry.chemical_compound chemistry Butanediol Yield (chemistry) Organic chemistry Stereoselectivity General Medicine Stereocenter
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200024035
Popis:	Chiral auxiliaries previously prepared from (-)-β---pinene (3), alcohols 5a-e and 6, were transformed into β---ketobutyrates 7a-e and 8 respectively. These compounds were stereoselectively reduced by NaBH4 in the presence of additives (MnCl2 or CaCl2), leading to the corresponding β-hydroxy butyrates 10a-e and 11 in good chemical yield and poor to moderate stereoselectivities (de 0%-60%). The configuration at the newly generated stereogenic center in 10a was determined to be S through its transformation into S-(+)-butanediol.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1205fe85a5dc0094c894c6786cd39f44 https://doi.org/10.1002/chin.200024035 Zobrazit plný text záznamu Plný text