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A general catalytic addition of nitromethane to simple N-diphenylphosphinoyl ketimines is achieved using either 10mol% 1,1,3,3-tetramethylguanidine (TMG) or 10mol% phosphazene (t-Bu-P1) as organic base catalysts in good to high yields. On the other hand, N-sulfinylketimines also furnished the aza-Henry product in good yield with moderate diastereoselectivity (3:1). Thus, the methodology developed...
A highly efficient synthesis of indolizidine (−)-209D I has been accomplished. The key reaction in the synthesis is the palladium(0)/benzoic acid catalyzed intramolecular hydroamination of the ε-amino alkyne 6. The excellent diastereoselectivity in the intramolecular hydroamination is discussed on the basis of the proposed transition state.
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