Brown, Jack A., Chudasama, Vijay, Giles, Melvyn E., Gill, Duncan M., Keegan, Phillip S., Kerr, William J., Munday, Rachel, Griffin, Karen and Watts, Andrew (2012) E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates. Organic & Biomolecular Chemistry, 10 (3). pp. 509-511. ISSN 1477-0520

Treatment of glycidyl sulfonamides with LDA delivers the corresponding enesulfonamide with good selectivity for the E-isomer, whereas the corresponding carbamates exhibit selectivity for the Z-enecarbamate. An E1cB elimination mechanism proceeding from a substrate–base chelate complex is advanced as rationalisation of the latter set of Z-selective outcomes.

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