Chemoselective addition of isocyanides to N-tert-butanesulfinimines

Guido V Janssen; Elwin Janssen; Christophe M L Vande Velde; Andreas W Ehlers; J Chris Slootweg; Eelco Ruijter; Koop Lammertsma; Romano V A Orru

doi:10.1021/ol502463s

Chemoselective addition of isocyanides to N-tert-butanesulfinimines

Guido V Janssen, Elwin Janssen, Christophe M L Vande Velde, Andreas W Ehlers, J Chris Slootweg, Eelco Ruijter, Koop Lammertsma, Romano V A Orru

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

Abstract

The reaction of isocyanides with N-tert-butanesulfinimines shows remarkable chemoselectivity. β-Sulfinylamino isocyanides are formed exclusively with aromatic sulfinimines, while α-sulfeneimino acetamides result when using aliphatic derivatives. A mechanism is suggested for the latter transformation, together with an explanation for the observed selectivity. Finally, a scope study is presented for this remarkably chemoselective reaction.

Original language	English
Pages (from-to)	5116-5119
Number of pages	4
Journal	Organic letters
Volume	16
Issue number	19
Early online date	17 Sept 2014
DOIs	https://doi.org/10.1021/ol502463s
Publication status	Published - 3 Oct 2014

Keywords

Acetamides/chemical synthesis
Catalysis
Cyanides/chemistry
Imines/chemical synthesis
Molecular Structure
Stereoisomerism
Sulfonium Compounds/chemical synthesis

UN SDGs

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

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10.1021/ol502463s

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CCDC 1019913: Experimental Crystal Structure Determination
Janssen, G. V. (Contributor), Janssen, E. (Contributor), Velde, C. M. L. V. (Contributor), Ehlers, A. W. (Contributor), Slootweg, J. C. (Contributor), Ruijter, E. (Contributor), Lammertsma, K. (Contributor) & Orru, R. V. A. (Contributor), Unknown Publisher, 3 Oct 2014
DOI: 10.5517/cc1379f2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1379f2&sid=DataCite
Dataset
CCDC 1019912: Experimental Crystal Structure Determination
Janssen, G. V. (Contributor), Janssen, E. (Contributor), Velde, C. M. L. V. (Contributor), Ehlers, A. W. (Contributor), Slootweg, J. C. (Contributor), Ruijter, E. (Contributor), Lammertsma, K. (Contributor) & Orru, R. V. A. (Contributor), Unknown Publisher, 3 Oct 2014
DOI: 10.5517/cc1379d1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1379d1&sid=DataCite
Dataset

Cite this

@article{1a21341921374e978e460c6f1af76811,

title = "Chemoselective addition of isocyanides to N-tert-butanesulfinimines",

abstract = "The reaction of isocyanides with N-tert-butanesulfinimines shows remarkable chemoselectivity. β-Sulfinylamino isocyanides are formed exclusively with aromatic sulfinimines, while α-sulfeneimino acetamides result when using aliphatic derivatives. A mechanism is suggested for the latter transformation, together with an explanation for the observed selectivity. Finally, a scope study is presented for this remarkably chemoselective reaction. ",

keywords = "Acetamides/chemical synthesis, Catalysis, Cyanides/chemistry, Imines/chemical synthesis, Molecular Structure, Stereoisomerism, Sulfonium Compounds/chemical synthesis",

author = "Janssen, {Guido V} and Elwin Janssen and {Vande Velde}, {Christophe M L} and Ehlers, {Andreas W} and Slootweg, {J Chris} and Eelco Ruijter and Koop Lammertsma and Orru, {Romano V A}",

year = "2014",

month = oct,

day = "3",

doi = "10.1021/ol502463s",

language = "English",

volume = "16",

pages = "5116--5119",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Chemoselective addition of isocyanides to N-tert-butanesulfinimines

AU - Janssen, Guido V

AU - Janssen, Elwin

AU - Vande Velde, Christophe M L

AU - Ehlers, Andreas W

AU - Slootweg, J Chris

AU - Ruijter, Eelco

AU - Lammertsma, Koop

AU - Orru, Romano V A

PY - 2014/10/3

Y1 - 2014/10/3

N2 - The reaction of isocyanides with N-tert-butanesulfinimines shows remarkable chemoselectivity. β-Sulfinylamino isocyanides are formed exclusively with aromatic sulfinimines, while α-sulfeneimino acetamides result when using aliphatic derivatives. A mechanism is suggested for the latter transformation, together with an explanation for the observed selectivity. Finally, a scope study is presented for this remarkably chemoselective reaction.

AB - The reaction of isocyanides with N-tert-butanesulfinimines shows remarkable chemoselectivity. β-Sulfinylamino isocyanides are formed exclusively with aromatic sulfinimines, while α-sulfeneimino acetamides result when using aliphatic derivatives. A mechanism is suggested for the latter transformation, together with an explanation for the observed selectivity. Finally, a scope study is presented for this remarkably chemoselective reaction.

KW - Acetamides/chemical synthesis

KW - Catalysis

KW - Cyanides/chemistry

KW - Imines/chemical synthesis

KW - Molecular Structure

KW - Stereoisomerism

KW - Sulfonium Compounds/chemical synthesis

U2 - 10.1021/ol502463s

DO - 10.1021/ol502463s

M3 - Article

C2 - 25229182

SN - 1523-7060

VL - 16

SP - 5116

EP - 5119

JO - Organic letters

JF - Organic letters

IS - 19

ER -

Chemoselective addition of isocyanides to N-tert-butanesulfinimines

Abstract

Keywords

UN SDGs

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Datasets

CCDC 1019913: Experimental Crystal Structure Determination

CCDC 1019912: Experimental Crystal Structure Determination

Cite this