An Enantioselective Synthetic Route to cis-2,4-Disubstituted and 2,4-Bridged Piperidines
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چکیده
منابع مشابه
An enantioselective synthetic route to cis-2,4-disubstituted and 2,4-bridged piperidines.
A synthetic route to enantiopure cis-2,4-disubstituted and 2,4-bridged piperidines is reported, the key step being a stereoselective conjugate addition of an organocuprate to a phenylglycinol-derived unsaturated lactam bearing a substituent at the 8a-position.
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A practical synthetic route to enantiopure 5-substituted cis-decahydroquinolines has been developed, the key steps being a stereoselective cyclocondensation of 2-substituted 6-oxocyclohexenepropionates 2 with (R)-phenylglycinol, the stereoselective hydrogenation of the resulting unsaturated tricyclic lactams, and the stereoselective reductive cleavage of the oxazolidine ring.
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The straightforward enantioselective construction of the hydroquinoline ring system from 1,5-polycarbonyl derivatives, using (R)-phenyglycinol as a chiral latent form of ammonia, is reported. The process mimics the key steps believed to occur in nature in the biosynthesis of amphibian decahydroquinoline alkaloids. Diastereodivergent routes to enantiopure cis-2,5-disubstituted decahydroquinoline...
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2008
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo801172b