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Rapid, scalable assembly of stereochemically rich, mono- and bicyclic acyl sultams.

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.

SUBMITTER: Asad N

PROVIDER: S-EPMC4179432 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Rapid, scalable assembly of stereochemically rich, mono- and bicyclic acyl sultams.

Asad Naeem N Samarakoon Thiwanka B TB Zang Qin Q Loh Joanna K JK Javed Salim S Hanson Paul R PR

Organic letters 20131206 1

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 ...[more]

PMID: 24313225

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