Pyrrolidine rings are an important scaffold in many pharmaceutical compounds and natural products and therefore a simple synthetic method for their production is desirable.  One method involves [3+2] dipolar cycloaddition of azomethine ylides with dipolarophiles. Conventional methods to access stabilized azomethine ylide systems rely upon the condensation of alpha amino esters with aldehydes.  However, ylide systems which would directly afford pyrrolidine rings bearing a 5-alkenyl substituent are difficult to access with current methods.  This presentation will describe an efficient protocol for the synthesis of 5-vinyl substituted pyrrolidine rings via [3+2] dipolar cycloaddition.  The new route begins with the formation of an azomethine ylide from a primary amine and aldehyde. The initial results, optimization studies, and substrate scope expansion of the methodology will be discussed.  The protocol is operationally simple, high-yielding, and stereoselective.

New route to azomethine ylides to yield 5-vinyl substituted pyrrolidine rings via a [3+2] dipolar cycloaddition

244th National Meeting (2012)

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