Tetrahedron Letters p. 7159 - 7162 (1997)
Update date:2022-08-10
Topics:
Coppola, Brian P.
Noe, Mark C.
Hong, Sam Shih-Kuang
The regioselectivity of 1,3-dipolar cycloaddition reactions between mesoionic compounds with singly-tethered substitents is examined. The results with propiolate dipolarophiles are compared with other singly and doubly-tethered examples according to a model using an asynchronous, concerted transition state. The isolation and reaction of a novel, non-aryl substituted mesoionic compound 7 is reported. A regiodirected synthesis starting with N-(2-thiazolinyl)proline gives a complementary dihydropyrroline compared with the reaction between N-formylproline and alkyl propiolates.
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