Catalytic Asymmetric Synthesis of Cyclopentyl β-Amino Esters by [3+2] Cycloaddition of Enecarbamates with Electrophilic Metalloenolcarbene Intermediates.

Autor:	Deng Y; Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249, USA., Yglesias MV; Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249, USA., Arman H; Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249, USA., Doyle MP; Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249, USA. michael.doyle@utsa.edu.
Jazyk:	angličtina
Zdroj:	Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2016 Aug 16; Vol. 55 (34), pp. 10108-12. Date of Electronic Publication: 2016 Jul 08.
DOI:	10.1002/anie.201605438
Abstrakt:	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. (© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze:	MEDLINE
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