Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 31, Pages 10084-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja804021m
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Enantioenriched 3-pyrrolines have been synthesized by highly enantioselective Fesulphos-Cu-catalysed 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 axomethine ylides. This cycloaddition desulfonylation strategy has been applied as a key step in the enantioselective synthesis of a biologically active C-azanucleoside.
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