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 › peer-review

4 Citations (Scopus)

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
DOIs	https://doi.org/10.1021/ol502463s
Publication status	Published - 3 Oct 2014
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol502463s

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@article{c34f2fa160e14099843f86b6c76ef7fb,

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.",

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.}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

month = oct,

day = "3",

doi = "10.1021/ol502463s",

language = "English",

volume = "16",

pages = "5116--5119",

journal = "Organic Letters",

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number = "19",

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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.

UR - http://www.scopus.com/inward/record.url?scp=84907706361&partnerID=8YFLogxK

U2 - 10.1021/ol502463s

DO - 10.1021/ol502463s

M3 - Article

C2 - 25229182

AN - SCOPUS:84907706361

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

ASJC Scopus subject areas

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