Diastereoselective allylations of allyl-propargyl hybrid cations: synthesis of conjugated 1,5-dien-7-yne frameworks bearing C(4)-stereogenic centers

Autor:	Toshiaki Aikawa, Teruhiko Ishikawa, Yumiko Mori, Seiki Saito
Rok vydání:	2004
Předmět:	Stereochemistry Chemistry Organic Chemistry Propargyl General Medicine Physical and Theoretical Chemistry Conjugated system Biochemistry Stereocenter
Zdroj:	Organic letters. 6(9)
ISSN:	1523-7060
Popis:	[reaction: see text] Chiral C(4)-substituted (E)- or (Z)-1-alkynyl-1-trimethylsilyloxy-2-butene systems provide anti-(Z) or syn-(Z) conjugated dienyne, with a very high level of stereocontrol, on treatment with BF(3).OEt(2) in CH(2)Cl(2) at -50 degrees C in the presence of allyltrimethylsilane. The Cieplak conformation for (E)-substrates and neighboring-group participation for (Z)-substrates are considered to be responsible for the stereochemical consequences.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2860b49912db977bf1740b919c29b2a7 https://pubmed.ncbi.nlm.nih.gov/15101744 Zobrazit plný text záznamu