Rapid, scalable assembly of stereochemically rich, mono- and bicyclic acyl sultams
Naeem Asad1, Thiwanka B Samarakoon, Qin Zang
1Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States , and The University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD) , 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States.
Abstract:
A one-pot, sequential protocol is reported that involves complementary ambiphile pairing (CAP) of a vinyl sulfonamide with a variety of unprotected amino acids via aza-Michael addition and subsequent intramolecular amidation. The method generates diverse, sp(3)-rich mono- and bicyclic acyl sultams in a highly scalable manner. Modular pairing of stereochemically rich building blocks allows quick access to all possible isomers. Extension to include one-pot, sequential 3-, 4-, and 5-multicomponent protocols is also discussed.
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