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The diastereoselective Mizoroki-Heck reaction of N-benzylpyrrolidines that incorporate a protected allylic alcohol moiety allows the synthesis of enantiomerically pure pyrrolo(1,2-b)isoquinolines, generating a tertiary stereocenter. The best results were obtained with the use of bulky phosphanes, as P(o-Tol)3. When a good leaving group, such as pivaloyl is used as a protecting group, the trans-10-vinyl substituted pyrroloisoquinoline (10S,10aS)-2a is obtained as the major diastereoisomer in moderate yield. On the other hand, when the allylic alcohol is protected as a silyl ether, the protected alcohol is retained, obtaining an enol ether, whichafter deprotection and reduction leads to the trans-10-hydroxymethyl substituted pyrrolisoquinoline (10S,10aS)-5, in enantiomerically pure form, with complete diastereoselectivity.

Diastereoselective formation of tertiary stereocenters <em>via</em> Mizoroki-Heck reaction