Tetrahedron p. 4181 - 4198 (1996)
Update date:2022-08-05
Topics:
Porter, Ned A.
Carter, Randall L.
Mero, Christopher L.
Roepel, Michael G.
Curran, Dennis P.
The telomerization of several acrylamides, most containing chiral auxiliary groups, was investigated. The first-formed stereogenic center in the n = 2 telomer (the penultimate center) has a significant effect on the configuration of the second (ultimate) center in the product. The penultimate chiral center of oxazolidine-derived acrylamides directs the configuration of the ultimate center such that the erythro n = 2 product is preferred. Sultam-substituted acrylamides preferentially lead, on the other hand, to threo products or give products with little stereoselectivity.
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