Recently we have developed a catalytic version of the aza-Cope rearrangement�Mannich cyclization using boron trifluoride.  One unique feature of the catalytized reaction is that it is often highly diastereoselective in spite of the conformational mobility of the substrates.  To explore the versatility of this process, we have examined the effect of varying the steric and electronic demands of the amine protecting group on reaction diastereoselectivity.  Furthermore, we have applied these conditions to the synthesis of 2,4- and 3,4-disubstituted pyrrolidines and as well as 2,3,4-trisubstituted pyrrolidines.

Influencing diastereoselectivity in the aza-Cope rearrangement—Mannich cyclization

245th National Meeting (2013)

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