Asymmetric ion pair catalysis of 6π electrocyclizations: Brønsted acid catalyzed enantioselective synthesis of optically active 1,4-dihydropyridazines

Arindam Das; Chandra M.R. Volla; Iuliana Atodiresei; Wolfgang Bettray; Magnus Rueping

doi:10.1002/anie.201301638

Asymmetric ion pair catalysis of 6π electrocyclizations: Brønsted acid catalyzed enantioselective synthesis of optically active 1,4-dihydropyridazines

Arindam Das, Chandra M.R. Volla, Iuliana Atodiresei, Wolfgang Bettray, Magnus Rueping^*

^*Corresponding author for this work

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

56 Scopus citations

Abstract

Electric slide: Described is a general, operationally simple, highly enantioselective Brønsted acid catalyzed condensation/6π- electrocyclization reaction between hydrazones and α,β-unsaturated aldehydes that yields valuable 1,4-dihydropyridazines. The reaction exhibits high tolerance towards functional groups and affords products with up to 98 % ee.

Original language	English (US)
Pages (from-to)	8008-8011
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	31
DOIs	https://doi.org/10.1002/anie.201301638
State	Published - Jul 29 2013
Externally published	Yes

Keywords

Brønsted acid
electrocyclic reactions
heterocycles
reaction mechanisms
synthetic methods

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.201301638

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title = "Asymmetric ion pair catalysis of 6π electrocyclizations: Br{\o}nsted acid catalyzed enantioselective synthesis of optically active 1,4-dihydropyridazines",

abstract = "Electric slide: Described is a general, operationally simple, highly enantioselective Br{\o}nsted acid catalyzed condensation/6π- electrocyclization reaction between hydrazones and α,β-unsaturated aldehydes that yields valuable 1,4-dihydropyridazines. The reaction exhibits high tolerance towards functional groups and affords products with up to 98 % ee.",

keywords = "Br{\o}nsted acid, electrocyclic reactions, heterocycles, reaction mechanisms, synthetic methods",

author = "Arindam Das and Volla, {Chandra M.R.} and Iuliana Atodiresei and Wolfgang Bettray and Magnus Rueping",

year = "2013",

month = jul,

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doi = "10.1002/anie.201301638",

language = "English (US)",

volume = "52",

pages = "8008--8011",

journal = "Angewandte Chemie - International Edition",

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publisher = "Wiley",

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}

Asymmetric ion pair catalysis of 6π electrocyclizations: Brønsted acid catalyzed enantioselective synthesis of optically active 1,4-dihydropyridazines. / Das, Arindam; Volla, Chandra M.R.; Atodiresei, Iuliana et al.
In: Angewandte Chemie - International Edition, Vol. 52, No. 31, 29.07.2013, p. 8008-8011.

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

TY - JOUR

T1 - Asymmetric ion pair catalysis of 6π electrocyclizations

T2 - Brønsted acid catalyzed enantioselective synthesis of optically active 1,4-dihydropyridazines

AU - Das, Arindam

AU - Volla, Chandra M.R.

AU - Atodiresei, Iuliana

AU - Bettray, Wolfgang

AU - Rueping, Magnus

PY - 2013/7/29

Y1 - 2013/7/29

N2 - Electric slide: Described is a general, operationally simple, highly enantioselective Brønsted acid catalyzed condensation/6π- electrocyclization reaction between hydrazones and α,β-unsaturated aldehydes that yields valuable 1,4-dihydropyridazines. The reaction exhibits high tolerance towards functional groups and affords products with up to 98 % ee.

AB - Electric slide: Described is a general, operationally simple, highly enantioselective Brønsted acid catalyzed condensation/6π- electrocyclization reaction between hydrazones and α,β-unsaturated aldehydes that yields valuable 1,4-dihydropyridazines. The reaction exhibits high tolerance towards functional groups and affords products with up to 98 % ee.

KW - Brønsted acid

KW - electrocyclic reactions

KW - heterocycles

KW - reaction mechanisms

KW - synthetic methods

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U2 - 10.1002/anie.201301638

DO - 10.1002/anie.201301638

M3 - Article

C2 - 23788474

AN - SCOPUS:84880837990

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SP - 8008

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 31

ER -

Asymmetric ion pair catalysis of 6π electrocyclizations: Brønsted acid catalyzed enantioselective synthesis of optically active 1,4-dihydropyridazines

Abstract

Keywords

ASJC Scopus subject areas

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