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

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10.1021/jo500790n

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@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",

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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

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