Abstract
Short routes to chiral 2-substituted pyrrolidines based on rhodium-catalyzed
hydroformylations of allylamines and their N -alkyl
and N -acyl derivatives, which were prepared
by asymmetric allylic substitutions, are described. The outcome
of the hydroformylation reaction was controlled by the substituent
at nitrogen, not by the substituent at carbon. In the case of N -alkylallylamines in situ reduction
to the pyrrolidines occurred, with N -acyl
derivatives hemiaminals and with primary amines cyclic imines were
formed. Very short syntheses of (S )-nicotine
and the alkaloid 225C are presented.
Key words
domino reactions - hydroformylation - pyrrolidines - alkaloids - cyclizations
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