A general synthetic route to enantiopure 5-substituted cis-decahydroquinolines.
نویسندگان
چکیده
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.
منابع مشابه
Enantio- and diastereoconvergent cyclocondensation reactions: synthesis of enantiopure cis-decahydroquinolines.
Up to four stereocenters with a well-defined configuration are generated in a single synthetic step by the cyclocondensation of (R)-phenylglycinol or (1S,2R)-1-amino-2-indanol with stereoisomeric mixtures (racemates, meso forms, diastereoisomers) of cyclohexanone-based δ-keto-acid and δ-keto-diacid derivatives in enantio- and diastereoconvergent processes that involve dynamic kinetic resolution...
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ورودعنوان ژورنال:
- The Journal of organic chemistry
دوره 74 4 شماره
صفحات -
تاریخ انتشار 2009