title: Catalytic Asymmetric Synthesis of Cyclopentyl β-Amino Esters by [3+2] Cycloaddition of Enecarbamates with Electrophilic Metalloenolcarbene Intermediates.
abstract: Chiral cyclopentyl β-amino esters are formed catalytically by [3+2] cycloaddition reactions of enecarbamates with electrophilic metalloenolcarbenes in high yield with up to 98 % ee and excellent diastereocontrol. Use of β-silyl-substituted enoldiazoacetates with a chiral dirhodium catalyst and trans-β-arylvinylcarbamates are optimal for this transformation, which occurs with hydrogen-bond association between the vinylcarbamate and the intermediate metalloenolcarbene. Reductive conversion of the protected amino esters forms highly functionalized cyclopentyl β-amino acids and 3-aminocyclopentanones.
authors.affiliation: Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249, USA.
authors.forename: Yongming
authors.initials: Y
authors.lastname: Deng
authors.affiliation: Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249, USA.
authors.forename: Matthew V
authors.initials: MV
authors.lastname: Yglesias
authors.affiliation: Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249, USA.
authors.forename: Hadi
authors.initials: H
authors.lastname: Arman
authors.affiliation: Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249, USA. michael.doyle@utsa.edu.
authors.forename: Michael P
authors.identifier: 0000-0003-1386-3780
authors.initials: MP
authors.lastname: Doyle
keywords: amino acids; cycloaddition; diazo compounds; enantioselectivity; rhodium