ol403070w_si_001.pdf (2.36 MB)
Rapid, Scalable Assembly of Stereochemically Rich, Mono- and Bicyclic Acyl Sultams
journal contribution
posted on 2014-01-03, 00:00 authored by Naeem Asad, Thiwanka B. Samarakoon, Qin Zang, Joanna K. Loh, Salim Javed, Paul R. HansonA 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, sp3-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.