SmI2-induced cyclization of (E)- and (Z)-β-alkoxyvinyl sulfones with aldehydes

Autor:	Tadashi Nakata, Tomohiro Kimura
Rok vydání:	2010
Předmět:	Inorganic Chemistry chemistry.chemical_classification Stereochemistry Chemistry Organic Chemistry Convergent synthesis Stereoselectivity Physical and Theoretical Chemistry Aldehyde Catalysis
Zdroj:	Tetrahedron: Asymmetry. 21:1389-1395
ISSN:	0957-4166
Popis:	SmI 2 -induced reaction of ( E )- and (Z)-β-alkoxyvinyl sulfones onto an aldehyde function afforded 2,6- syn -2,3- trans - and 2,6- syn -2,3- cis -tetrahydropyran-3-ols, respectively, via stereoselective cyclization. This reaction was applied to the synthesis of 2-methyl-tetrahydropyran, corresponding to the N-ring of gymnocin-A, and 2- exo -methylene-tetrahydropyran, a key intermediate for convergent synthesis of polycyclic ethers based on the Suzuki–Miyaura reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7e6f369160e8f37aee271ecd0989e8e8 https://doi.org/10.1016/j.tetasy.2010.04.066 Zobrazit plný text záznamu Full Text from ScienceDirect