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Indeed, we were delighted to find that translation to solid phase proved largely uneventful for the majority of these reactions. Consistent with our solution-phase results, Krische and coworkers¡¯ Rh(I)¨C2,2¡ä-bis(diphenylphosphino)-1,1¡ä-binaphthyl (BINAP) catalyzed reductive cyclization (21) proceeded with reagent-controlled diastereoselectivity for 3a,b, but not for 3d, affording access to both exo-pyrroline relative diastereomers 6a,b and 6¡äa,b and the major diastereomer 6d (Scheme 2). The yields and diastereoselectivities were comparable to those observed in the original solution-phase studies in this first application to solid-phase synthesis. Enynes 3a,b,d also underwent Evans et al.¡¯s diastereoselective Rh(I)-catalyzed [4 + 2 + 2] reaction with 1,3-butadiene successfully successfully (22). This reaction has not previously been used in solidphase synthesis and, based on our previous solution-phase studies, the sulfinamides were oxidized to the corresponding sulfonamides prior to cycloaddition, leading to cyclooctapyrrolidines 7a,b,d.

[ Last edited by Mally89 on 2011-6-17 at 20:52 ]

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