Efficient and highly diastereoselective preparation of a myrtenal derived bis-sulfoxide and its preliminary evaluation as chiral acyl donor

Autor:	L. Gerardo Zepeda, M. Elena Vargas-Dı́az, Selene Lagunas-Rivera, Pedro Joseph-Nathan, Joaquuin Tamariz
Rok vydání:	2005
Předmět:	Benzaldehyde chemistry.chemical_compound Chiral auxiliary chemistry Stereochemistry Organic Chemistry Drug Discovery Absolute configuration Disulfide bond Sulfoxide Biochemistry Single crystal
Zdroj:	Tetrahedron Letters. 46:3297-3300
ISSN:	0040-4039
Popis:	Treatment of disulfide 7 with NaIO 4 in EtOH at rt gave monosulfoxide 8 (95%), while at 50 °C it gave trans -bis-sulfoxide 6a (84%, >99% de). In contrast, treatment of 7 with MCPBA gave bis-sulfone 9 (95%). The anion of 6a reacted with benzaldehyde affording carbinol 10 (76%, >99% de). The absolute configuration of 8 , 6a , and 10 was established by single crystal X-ray diffraction analyses.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::381b5e7c7a2990d765304251907ad38c https://doi.org/10.1016/j.tetlet.2005.03.104 Zobrazit plný text záznamu Full Text from ScienceDirect