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Palladium[0]-mediated aminospirocyclization of tertiary allylic sulfones. Stereospecific construction of the azabicyclic ring system of cephalotaxine
Journal article   Peer reviewed

Palladium[0]-mediated aminospirocyclization of tertiary allylic sulfones. Stereospecific construction of the azabicyclic ring system of cephalotaxine

Zhendong Jin and F.L Puchs
Tetrahedron letters, Vol.37(30), pp.5253-5256
1996
DOI: 10.1016/0040-4039(96)01112-4

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Abstract

Tertiary allylic sulfones which bear a secondary aminopropyl moiety undergo smooth palladium [0]-mediated spirocyclization. The reaction proceeds via a π-allyl intermediate and the resultant azabicyclic product is formed with net retention of sulfone stereochemistry. The use of tetramethylguanidine as companion base is required for high yielding reactions. Graphic

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