Enantiopure erythro- and threo-1-aryl-1-[2-pyrrolidyl]-methanols: synthesis from l-proline

Autor:	Khalid Azyat, Michel Schmitt, Arlette Solladié-Cavallo, Richard Welter
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Chemistry Stereochemistry Aryl Organic Chemistry Diastereomer Alcohol Aldehyde Catalysis Inorganic Chemistry chemistry.chemical_compound Enantiopure drug Alcohol oxidation Swern oxidation Physical and Theoretical Chemistry Racemization
Zdroj:	Tetrahedron: Asymmetry. 16:1055-1060
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2005.01.010
Popis:	Enantiopure (1R,2S)-erythro- and (1S,2S)-threo-isomers of four new aryl-pyrrolidyl alcohols 5aH, 5aMe, 5bH and 5bMe have been obtained in five steps from (−)-(S)-proline and fully characterized. The oxidation of alcohol 8 into aldehyde 9 was the most difficult step and racemization occurs during Swern oxidation but this difficulty can be overcome by using SO3/pyridine as oxidant. Diastereomer I of the protected amino alcohol 10a crystallized and was shown to be the (1R,2S)-erythro-isomer (e-10a-I) using X-ray crystallography. Therefore the (1R,2S)-erythro structure was assigned to all compounds obtained from e-10a-I, and, as a consequence, the (1S,2S)-threo structure was assigned to diastereomers II.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d90a3ee066d3d66ef3204e3a8de87117 https://doi.org/10.1016/j.tetasy.2005.01.010 Zobrazit plný text záznamu Full Text from ScienceDirect