Bis-sulfonyl ethylene as masked acetylene equivalent in catalytic asymmetric [3 + 2] cycloaddition of azomethine ylides.

Abstract

Enantioenriched 3-pyrrolines have been synthesized by highly enantioselective Fesulphos-Cu-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with trans-1,2-bisphenylsulfonyl ethylene, followed by reductive sulfonyl elimination. High levels of reactivity, exoselectivity, and enantioselectivity have been accomplished for a variety of substituted azomethine ylides. This cycloaddition-desulfonylation strategy has been applied as a key step in the enantioselective synthesis of a biologically active C-azanucleoside.

DOI: 10.1021/ja804021m

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Cite this paper

@article{LpezPrez2008BissulfonylEA, title={Bis-sulfonyl ethylene as masked acetylene equivalent in catalytic asymmetric [3 + 2] cycloaddition of azomethine ylides.}, author={Ana M L{\'o}pez-P{\'e}rez and Javier Adrio and Juan C Carretero}, journal={Journal of the American Chemical Society}, year={2008}, volume={130 31}, pages={10084-5} }