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

Research output: Contribution to journal › Article › 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.

Original language	English
Pages (from-to)	4078-4081
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	16
DOIs	https://doi.org/10.1021/ol3017066
Publication status	Published - 17 Aug 2012
Externally published	Yes

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10.1021/ol3017066

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title = "Noncovalent organocatalytic synthesis of enantioenriched terminal aziridines with a quaternary stereogenic center",

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",

language = "English",

volume = "14",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

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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.

UR - https://www.scopus.com/pages/publications/84865228389

U2 - 10.1021/ol3017066

DO - 10.1021/ol3017066

M3 - Article

SN - 1523-7060

VL - 14

SP - 4078

EP - 4081

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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