Unprecedented reactivity in the Morita-Baylis-Hillman reaction; intramolecular alpha-alkylation of enones using saturated alkyl halides.
نویسندگان
چکیده
sp3 Hybridized electrophiles, never before used in the organomediated Morita-Baylis-Hillman reaction, now facilitate the formation of five- and six-membered enone cycloalkylation products.
منابع مشابه
Influence of Michael acceptor stereochemistry on intramolecular Morita-Baylis-Hillman reactions.
[reaction: see text] A study of the effect of Michael acceptor stereochemistry on the efficiency of intramolecular Morita-Baylis-Hillman (MBH) reactions has been performed. The reactions were catalyzed by a phosphine, and the reaction substrates studied were enones containing a pendant aldehyde moiety attached at the beta-position of the alkene group. In all cases examined with PPh3 as the cata...
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In this study we performed the total synthesis of the terpene indole alkaloid (+)-ibophyllidine through a pathway involving asymmetric phosphine catalysis, with our novel l-4-hydroxyproline-derived chiral phosphine mediating the key [3 + 2] annulation. Hydrogenation of the [3 + 2] adduct allowed the rapid formation of the stereochemically dense pyrrolidine ring of (+)-ibophyllidine in excellent...
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ورودعنوان ژورنال:
- Chemical communications
دوره 46 شماره
صفحات -
تاریخ انتشار 2005