Concise Synthesis of Optically Active Cyclopropane β-Amino Acid Derivatives via Olefination of Cyclopropanone
Myunggi Jung1,2, Vincent N G Lindsay1
1Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States.
Abstract:
An expedient synthesis of cyclopropane β-amino acid derivatives is reported from readily accessible cyclopropanone surrogates. The addition of stabilized phosphorus ylides to 1-sulfonylcyclopropanols leads to the formation of highly electrophilic alkylidenecyclopropanes shown to be reactive in a telescopic aza-Michael reaction, in mild conditions. The transformation proceeds with complete diastereocontrol in favor of the trans products and is amenable to the rapid production of highly enantioenriched β-amino acid derivatives, peptidomimetics and spirocyclic analogues.
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