Stereoselective synthesis of N-aryl proline amides by biotransformation-Ugi-Smiles sequence

Anass Znabet; Sara Blanken; Elwin Janssen; Frans J J de Kanter; Madeleine Helliwell; Nicholas J Turner; Eelco Ruijter; Romano V A Orru

doi:10.1039/c1ob06699d

Stereoselective synthesis of N-aryl proline amides by biotransformation-Ugi-Smiles sequence

Anass Znabet
, Sara Blanken
, Elwin Janssen
, Frans J J de Kanter
, Madeleine Helliwell
, Nicholas J Turner
, Eelco Ruijter
, Romano V A Orru

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

An efficient combination of MAO-N-catalyzed desymmetrization of cyclic meso-amines with Ugi-Smiles multicomponent chemistry produced optically pure N-aryl proline amides. This method represents the first report of a fully asymmetric Ugi-Smiles process.

Original language	English
Pages (from-to)	941-944
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	5
DOIs	https://doi.org/10.1039/c1ob06699d
Publication status	Published - 7 Feb 2012

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This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 6 Clean Water and Sanitation

Keywords

Amides/chemical synthesis
Amines/chemical synthesis
Catalysis
Cyclization
Models, Molecular
Proline/chemical synthesis
Stereoisomerism

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10.1039/c1ob06699d

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CCDC 844264: Experimental Crystal Structure Determination
Znabet, A. (Contributor), Blanken, S. (Contributor), Janssen, E. (Contributor), De Kanter, F. J. J. (Contributor), Helliwell, M. (Contributor), Turner, N. J. (Contributor), Ruijter, E. (Contributor) & Orru, R. V. A. (Contributor), Unknown, 1 Jan 2012
DOI: 10.5517/ccxbjb2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccxbjb2&sid=DataCite
Dataset / Software: Dataset

Cite this

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title = "Stereoselective synthesis of N-aryl proline amides by biotransformation-Ugi-Smiles sequence",

abstract = "An efficient combination of MAO-N-catalyzed desymmetrization of cyclic meso-amines with Ugi-Smiles multicomponent chemistry produced optically pure N-aryl proline amides. This method represents the first report of a fully asymmetric Ugi-Smiles process.",

keywords = "Amides/chemical synthesis, Amines/chemical synthesis, Catalysis, Cyclization, Models, Molecular, Proline/chemical synthesis, Stereoisomerism",

author = "Anass Znabet and Sara Blanken and Elwin Janssen and \{de Kanter\}, \{Frans J J\} and Madeleine Helliwell and Turner, \{Nicholas J\} and Eelco Ruijter and Orru, \{Romano V A\}",

year = "2012",

month = feb,

day = "7",

doi = "10.1039/c1ob06699d",

language = "English",

volume = "10",

pages = "941--944",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "5",

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TY - JOUR

T1 - Stereoselective synthesis of N-aryl proline amides by biotransformation-Ugi-Smiles sequence

AU - Znabet, Anass

AU - Blanken, Sara

AU - Janssen, Elwin

AU - de Kanter, Frans J J

AU - Helliwell, Madeleine

AU - Turner, Nicholas J

AU - Ruijter, Eelco

AU - Orru, Romano V A

PY - 2012/2/7

Y1 - 2012/2/7

N2 - An efficient combination of MAO-N-catalyzed desymmetrization of cyclic meso-amines with Ugi-Smiles multicomponent chemistry produced optically pure N-aryl proline amides. This method represents the first report of a fully asymmetric Ugi-Smiles process.

AB - An efficient combination of MAO-N-catalyzed desymmetrization of cyclic meso-amines with Ugi-Smiles multicomponent chemistry produced optically pure N-aryl proline amides. This method represents the first report of a fully asymmetric Ugi-Smiles process.

KW - Amides/chemical synthesis

KW - Amines/chemical synthesis

KW - Catalysis

KW - Cyclization

KW - Models, Molecular

KW - Proline/chemical synthesis

KW - Stereoisomerism

U2 - 10.1039/c1ob06699d

DO - 10.1039/c1ob06699d

M3 - Article

C2 - 22179495

SN - 1477-0520

VL - 10

SP - 941

EP - 944

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 5

ER -

Stereoselective synthesis of N-aryl proline amides by biotransformation-Ugi-Smiles sequence

Abstract

UN SDGs

Keywords

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Datasets

CCDC 844264: Experimental Crystal Structure Determination

Cite this