Chemoselective addition of isocyanides to N-tert-butanesulfinimines

Research output: Contribution to JournalArticleAcademicpeer-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 languageEnglish
Pages (from-to)5116-5119
Number of pages4
JournalOrganic Letters
Volume16
Issue number19
Early online date17 Sep 2014
DOIs
Publication statusPublished - 3 Oct 2014

Fingerprint

Cyanides
Acetamides
selectivity
Derivatives
sulfinimine

Keywords

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

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 = "10",
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",

}

Chemoselective addition of isocyanides to N-tert-butanesulfinimines. / Janssen, Guido V; Janssen, Elwin; Vande Velde, Christophe M L; Ehlers, Andreas W; Slootweg, J Chris; Ruijter, Eelco; Lammertsma, Koop; Orru, Romano V A.

In: Organic Letters, Vol. 16, No. 19, 03.10.2014, p. 5116-5119.

Research output: Contribution to JournalArticleAcademicpeer-review

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

VL - 16

SP - 5116

EP - 5119

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 19

ER -