The first examples of Rh-catalyzed cyclohydrocarbonylation-bicyclization of N-allylic amides of arylacetic acids are reported. This novel carbonylative bicyclization process was successfully applied to the rapid syntheses of crispine A and its analogues (tricyclic indolizidine alkaloids) as well as harmicine (tetracyclic beta-carboline alkaloid).
Facile syntheses of enantiopure trans- and cis-3-hydroxypiperidine derivatives and 3-hydroxypipecolic acids are reported, featuring Rh-catalyzed cyclohydrocarbonylation through common intermediates. A diaxial conformation in a 2,3-disubstituted N-Boc-piperidinyl structure is revealed by an X-ray crystallographic analysis.
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