Noncovalent organocatalytic synthesis of enantioenriched terminal aziridines with a quaternary stereogenic center

Claudia De Fusco; Tiziana Fuoco; Gianluca Croce; Alessandra Lattanzi

doi:10.1021/ol3017066

Noncovalent organocatalytic synthesis of enantioenriched terminal aziridines with a quaternary stereogenic center

Claudia De Fusco, Tiziana Fuoco, Gianluca Croce, Alessandra Lattanzi

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of α-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable α,α-disubstituted α-amino acid esters has been demonstrated.

Lingua originale	Inglese
pagine (da-a)	4078-4081
Numero di pagine	4
Rivista	Organic Letters
Volume	14
Numero di pubblicazione	16
DOI	https://doi.org/10.1021/ol3017066
Stato di pubblicazione	Pubblicato - 17 ago 2012
Pubblicato esternamente	Sì

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10.1021/ol3017066

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abstract = "A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of α-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable α,α-disubstituted α-amino acid esters has been demonstrated.",

author = "{De Fusco}, Claudia and Tiziana Fuoco and Gianluca Croce and Alessandra Lattanzi",

year = "2012",

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doi = "10.1021/ol3017066",

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journal = "Organic Letters",

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T1 - Noncovalent organocatalytic synthesis of enantioenriched terminal aziridines with a quaternary stereogenic center

AU - De Fusco, Claudia

AU - Fuoco, Tiziana

AU - Croce, Gianluca

AU - Lattanzi, Alessandra

PY - 2012/8/17

Y1 - 2012/8/17

N2 - A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of α-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable α,α-disubstituted α-amino acid esters has been demonstrated.

AB - A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of α-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable α,α-disubstituted α-amino acid esters has been demonstrated.

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U2 - 10.1021/ol3017066

DO - 10.1021/ol3017066

M3 - Article

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JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Noncovalent organocatalytic synthesis of enantioenriched terminal aziridines with a quaternary stereogenic center

Abstract

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