A method for the synthesis of fluorinated beta'-amino beta-dicarbonyl compounds using a Zr-catalyzed Mannich-type reaction has been developed, starting from N-protected trifluoromethyl aldimines and cyclic or acyclic beta-keto esters bearing different ester residues. The in situ generated metallic complex reacted with optically pure trifluoromethyl aldimine derived from (R)-alpha-methylbenzylamine, giving a highly diastereoselective asymmetric Mannich-type addition with formation of a chiral quaternary center. The absolute configuration at the new chiral centers was assigned through two-dimensional nuclear Overhauser effect spectroscopic analysis coupled with computational studies.

Stereoselective ZrCl4-catalyzed mannich-type reaction of beta-keto Esters with chiral trifluoromethyl aldimines / Parise, Luca; Pellacani, Lucio; Sciubba, Fabio; Trulli, Laura; Fioravanti, Stefania. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 80:16(2015), pp. 8300-8306. [10.1021/acs.joc.5b01379]

Stereoselective ZrCl4-catalyzed mannich-type reaction of beta-keto Esters with chiral trifluoromethyl aldimines

PELLACANI, Lucio
Secondo
;
SCIUBBA, FABIO;TRULLI, LAURA
Penultimo
;
FIORAVANTI, Stefania
Ultimo
2015

Abstract

A method for the synthesis of fluorinated beta'-amino beta-dicarbonyl compounds using a Zr-catalyzed Mannich-type reaction has been developed, starting from N-protected trifluoromethyl aldimines and cyclic or acyclic beta-keto esters bearing different ester residues. The in situ generated metallic complex reacted with optically pure trifluoromethyl aldimine derived from (R)-alpha-methylbenzylamine, giving a highly diastereoselective asymmetric Mannich-type addition with formation of a chiral quaternary center. The absolute configuration at the new chiral centers was assigned through two-dimensional nuclear Overhauser effect spectroscopic analysis coupled with computational studies.
2015
mannich-type reactions; fluorinated compounds; stereoselectivity
01 Pubblicazione su rivista::01a Articolo in rivista
Stereoselective ZrCl4-catalyzed mannich-type reaction of beta-keto Esters with chiral trifluoromethyl aldimines / Parise, Luca; Pellacani, Lucio; Sciubba, Fabio; Trulli, Laura; Fioravanti, Stefania. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 80:16(2015), pp. 8300-8306. [10.1021/acs.joc.5b01379]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/854459
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