Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams

Xavier Companyó; Pierre Yves Geant; Andrea Mazzanti; Albert Moyano; Ramon Rios

doi:10.1016/j.tet.2013.11.028

Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams

Xavier Companyó
, Pierre Yves Geant
, Andrea Mazzanti
, Albert Moyano
, Ramon Rios

Chemistry

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

An organocatalytic enantioselective synthesis of α-methylene-γ- lactams has been developed. The reaction between protected 2-aminomalonates and Morita-Baylis-Hillman carbonates is catalyzed by chiral Lewis bases to afford the corresponding lactams in excellent yields and moderate to good enantioselectivities, after work-up.

Original language	British English
Pages (from-to)	75-82
Number of pages	8
Journal	Tetrahedron
Volume	70
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2013.11.028
State	Published - 7 Jan 2014

Keywords

Asymmetric synthesis
Lactams
Morita-Baylis-Hillman
One-pot reaction
Organocatalysis

Access to Document

10.1016/j.tet.2013.11.028

OpenUrl availability

Full text

Cite this

@article{f8d881ddae5c4461b53eb7784e8f1a3f,

title = "Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams",

abstract = "An organocatalytic enantioselective synthesis of α-methylene-γ- lactams has been developed. The reaction between protected 2-aminomalonates and Morita-Baylis-Hillman carbonates is catalyzed by chiral Lewis bases to afford the corresponding lactams in excellent yields and moderate to good enantioselectivities, after work-up.",

keywords = "Asymmetric synthesis, Lactams, Morita-Baylis-Hillman, One-pot reaction, Organocatalysis",

author = "Xavier Company{\'o} and Geant, \{Pierre Yves\} and Andrea Mazzanti and Albert Moyano and Ramon Rios",

note = "Funding Information: Financial support from the University of Southampton (to R.R.) and from the Universitat de Barcelona (to A.M.) is gratefully acknowledged. X.C. is grateful to MICINN for a PFU pre-doctoral fellowship. A.M. thanks the University of Bologna (RFO funds 2008). This work has been done under the auspices of COST Action CM0905 (ORCA). Financial support from European Regional Development Fund (ERDF) (AI-Chem \& InterReg IVb) is gratefully acknowledged (R.R.). ",

year = "2014",

month = jan,

day = "7",

doi = "10.1016/j.tet.2013.11.028",

language = "British English",

volume = "70",

pages = "75--82",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "1",

}

TY - JOUR

T1 - Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams

AU - Companyó, Xavier

AU - Geant, Pierre Yves

AU - Mazzanti, Andrea

AU - Moyano, Albert

AU - Rios, Ramon

N1 - Funding Information: Financial support from the University of Southampton (to R.R.) and from the Universitat de Barcelona (to A.M.) is gratefully acknowledged. X.C. is grateful to MICINN for a PFU pre-doctoral fellowship. A.M. thanks the University of Bologna (RFO funds 2008). This work has been done under the auspices of COST Action CM0905 (ORCA). Financial support from European Regional Development Fund (ERDF) (AI-Chem & InterReg IVb) is gratefully acknowledged (R.R.).

PY - 2014/1/7

Y1 - 2014/1/7

N2 - An organocatalytic enantioselective synthesis of α-methylene-γ- lactams has been developed. The reaction between protected 2-aminomalonates and Morita-Baylis-Hillman carbonates is catalyzed by chiral Lewis bases to afford the corresponding lactams in excellent yields and moderate to good enantioselectivities, after work-up.

AB - An organocatalytic enantioselective synthesis of α-methylene-γ- lactams has been developed. The reaction between protected 2-aminomalonates and Morita-Baylis-Hillman carbonates is catalyzed by chiral Lewis bases to afford the corresponding lactams in excellent yields and moderate to good enantioselectivities, after work-up.

KW - Asymmetric synthesis

KW - Lactams

KW - Morita-Baylis-Hillman

KW - One-pot reaction

KW - Organocatalysis

UR - https://www.scopus.com/pages/publications/84889671804

U2 - 10.1016/j.tet.2013.11.028

DO - 10.1016/j.tet.2013.11.028

M3 - Article

AN - SCOPUS:84889671804

SN - 0040-4020

VL - 70

SP - 75

EP - 82

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams

Abstract

Keywords

Access to Document

OpenUrl availability

Other files and links

Fingerprint

Cite this