Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines

Guido V. Janssen; Paul Slobbe; Maurice Mooijman; Art Kruithof; Andreas W. Ehlers; Célia Fonseca Guerra; F. Matthias Bickelhaupt; J. Chris Slootweg; Eelco Ruijter; Koop Lammertsma; Romano V.A. Orru

doi:10.1021/jo500790n

Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines

Guido V. Janssen, Paul Slobbe, Maurice Mooijman, Art Kruithof, Andreas W. Ehlers, Célia Fonseca Guerra, F. Matthias Bickelhaupt, J. Chris Slootweg, Eelco Ruijter, Koop Lammertsma, Romano V.A. Orru

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

6 Citations (Scopus)

Abstract

A convenient trans-selective one-pot synthesis of tetrafunctionalized 2-imidazolines is described. Our approach to these valuable heterocyclic scaffolds involves a formal 1,3-dipolar cycloaddition between nitrile ylides or nitrilium triflates and imines. A detailed experimental study in combination with a high-level computational exploration of reaction routes reveals a plausible reaction pathway that accounts for the observed diastereoselectivity.

Original language	English
Pages (from-to)	5219-5226
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	79
Issue number	11
DOIs	https://doi.org/10.1021/jo500790n
Publication status	Published - 6 Jun 2014
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo500790n

Cite this

@article{5156217a3b294778ace6f32c999f796b,

title = "Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines",

abstract = "A convenient trans-selective one-pot synthesis of tetrafunctionalized 2-imidazolines is described. Our approach to these valuable heterocyclic scaffolds involves a formal 1,3-dipolar cycloaddition between nitrile ylides or nitrilium triflates and imines. A detailed experimental study in combination with a high-level computational exploration of reaction routes reveals a plausible reaction pathway that accounts for the observed diastereoselectivity.",

author = "Janssen, \{Guido V.\} and Paul Slobbe and Maurice Mooijman and Art Kruithof and Ehlers, \{Andreas W.\} and Guerra, \{C{\'e}lia Fonseca\} and Bickelhaupt, \{F. Matthias\} and Slootweg, \{J. Chris\} and Eelco Ruijter and Koop Lammertsma and Orru, \{Romano V.A.\}",

year = "2014",

month = jun,

day = "6",

doi = "10.1021/jo500790n",

language = "English",

volume = "79",

pages = "5219--5226",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines

AU - Janssen, Guido V.

AU - Slobbe, Paul

AU - Mooijman, Maurice

AU - Kruithof, Art

AU - Ehlers, Andreas W.

AU - Guerra, Célia Fonseca

AU - Bickelhaupt, F. Matthias

AU - Slootweg, J. Chris

AU - Ruijter, Eelco

AU - Lammertsma, Koop

AU - Orru, Romano V.A.

PY - 2014/6/6

Y1 - 2014/6/6

N2 - A convenient trans-selective one-pot synthesis of tetrafunctionalized 2-imidazolines is described. Our approach to these valuable heterocyclic scaffolds involves a formal 1,3-dipolar cycloaddition between nitrile ylides or nitrilium triflates and imines. A detailed experimental study in combination with a high-level computational exploration of reaction routes reveals a plausible reaction pathway that accounts for the observed diastereoselectivity.

AB - A convenient trans-selective one-pot synthesis of tetrafunctionalized 2-imidazolines is described. Our approach to these valuable heterocyclic scaffolds involves a formal 1,3-dipolar cycloaddition between nitrile ylides or nitrilium triflates and imines. A detailed experimental study in combination with a high-level computational exploration of reaction routes reveals a plausible reaction pathway that accounts for the observed diastereoselectivity.

UR - https://www.scopus.com/pages/publications/84902094478

U2 - 10.1021/jo500790n

DO - 10.1021/jo500790n

M3 - Article

C2 - 24820129

AN - SCOPUS:84902094478

SN - 0022-3263

VL - 79

SP - 5219

EP - 5226

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -

Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this