Asymmetric synthesis of hexapropionate synthons by sequential enantiotopic group selective enolization of meso diketones

Autor:	Dale E. Ward, K Saravanan, M. Abdul Rasheed, Olukayode T. Akinnusi, H. Martin Gillis, Pradip K. Sasmal
Rok vydání:	2006
Předmět:	chemistry.chemical_classification Lithium amide Chemistry Organic Chemistry Synthon Enantioselective synthesis Biochemistry Medicinal chemistry Enol Aldehyde Kinetic resolution Stereocenter chemistry.chemical_compound Aldol reaction Physical and Theoretical Chemistry
Zdroj:	Organic letters. 8(12)
ISSN:	1523-7060
Popis:	Meso 1,9-diketones (six to seven stereocenters) are readily obtained by stepwise or simultaneous two-directional aldol reactions of tetrahydro-4H-thiopyran-4-one with a thiopyran-derived aldehyde or dialdehyde. Enantioselective enolizations of these diketones with the lithium amide from (R,R)-bis(1-phenylethyl)amine occur with simultaneous kinetic resolution to give the mono-TMS enol ethers in >90% yields (BORSM) and >95% ee. The products are applicable to polypropionate synthesis. [reaction: see text]
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a1fea8e6e046cc5be94a15daffbc6e68 https://pubmed.ncbi.nlm.nih.gov/16737331 Zobrazit plný text záznamu