A Combined Intramolecular Diels–Alder/Intramolecular Schmidt Reaction: Formal Synthesis of (±)-Stenine
نویسندگان
چکیده
منابع مشابه
Synthesis of crispine A analogues via an intramolecular Schmidt reaction
An intramolecular Schmidt reaction strategy for the synthesis of various derivatives of crispine A using azido-ketone as a key intermediate is described.
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Substituted pyrroles were prepared by a gold(I)-catalyzed acetylenic Schmidt reaction of homopropargyl azides. The reaction allows for regiospecific substitution at each position of the pyrrole ring under mild conditions. A mechanism in which azides serve as nucleophiles toward gold(I)-activated alkynes with subsequent gold(I)-aided expulsion of dinitrogen is proposed.
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The intramolecular Schmidt reaction of ketones and tethered azides is an efficient method for the generation of amides and lactams. This reaction is catalyzed by Lewis acids, which tightly bind the strongly basic amide product and result in product inhibition. We report herein conditions to achieve a catalytic Schmidt reaction using substoichiometric amounts of the heat-stable Lewis acid Sc(OTf...
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ژورنال
عنوان ژورنال: Angewandte Chemie International Edition
سال: 2002
ISSN: 1433-7851,1521-3773
DOI: 10.1002/1521-3773(20021115)41:22<4316::aid-anie4316>3.0.co;2-u