A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines

A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines

A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-hydroxyisoindolinones has been demonstrated in this communication. A variety of isoindolinone-based α-amino diazo esters bearing a quaternary stereogenic cent...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2018-04, Vol.54 (28), p.3516-3519
Hauptverfasser: Unhale, Rajshekhar A, Sadhu, Milon M, Ray, Sumit K, Biswas, Rayhan G, Singh, Vinod K
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Adducts
Esters
Imines
Phosphoric acid
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container_issue 28
container_start_page 3516
container_title Chemical communications (Cambridge, England)
container_volume 54
creator Unhale, Rajshekhar A
Sadhu, Milon M
Ray, Sumit K
Biswas, Rayhan G
Singh, Vinod K
description A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-hydroxyisoindolinones has been demonstrated in this communication. A variety of isoindolinone-based α-amino diazo esters bearing a quaternary stereogenic center were afforded in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the products has been depicted by the hydrogenation of the diazo moiety of adducts.
doi_str_mv 10.1039/C8CC01436A
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Adducts
Esters
Imines
Phosphoric acid
title A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines
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