Hetero Diels—Alder Type Reactions Between Danishefsky′s Dienes in the Presence of Lewis Base Catalysts. An Efficient Method for the Synthesis of Substituted 2,3-Dihydropyran-4-ones

Autor:	Takayuki Kitazawa, Teruaki Mukaiyama
Rok vydání:	2007
Předmět:	Pharmacology Silylation Dihydropyran Organic Chemistry General Medicine Methoxide Medicinal chemistry Analytical Chemistry Lewis acid catalysis Catalysis chemistry.chemical_compound chemistry Diels alder Alkoxy group Organic chemistry Moiety Lewis acids and bases
Zdroj:	ChemInform. 38
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200718129
Popis:	Alkoxy anion such as methoxide anion works effectively as Lewis base catalyst to activate silicon-carbon bond of 1-methoxy-3-trimethylsilyl-oxy-1,3-butadiens (Danishefsky's dienes) in the reaction between aldehydes and ketones. By using Lewis base as catalyst, acid sensitive substrates and Lewis basic moiety containing substrates can be used in this reaction. The hetero Diels-Alder type reaction proceeds through stepwise mechanism between silyl enolates and carbonyl compounds.
Databáze:	OpenAIRE
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