Asymmetric Brønsted acid catalyzed cycloadditions-efficient enantioselective synthesis of pyrazolidines, pyrazolines, and 1,3-diamines from N-acyl hyrazones and alkenes

Magnus Rueping; Modhu Sudan Maji; Hatice Baśpínar Küçük; Iuliana Atodiresei

doi:10.1002/anie.201205813

Asymmetric Brønsted acid catalyzed cycloadditions-efficient enantioselective synthesis of pyrazolidines, pyrazolines, and 1,3-diamines from N-acyl hyrazones and alkenes

Magnus Rueping^*, Modhu Sudan Maji, Hatice Baśpínar Küçük, Iuliana Atodiresei

^*Corresponding author for this work

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

82 Scopus citations

Abstract

A general, metal-free, highly enantioselective Bronsted acid catalyzed [3+2] cycloaddition between hydrazones and alkenes has been developed that affords pyrazolidine derivatives (see scheme). The resulting optically active pyrazolidines can undergo many chemical transformations which allow, for example, the enantioselective synthesis of valuable pyrazolines and 1,3-diamines.

Original language	English (US)
Pages (from-to)	12864-12868
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	51
DOIs	https://doi.org/10.1002/anie.201205813
State	Published - Dec 14 2012
Externally published	Yes

Keywords

heterocycles
homogeneous catalysis
hydrazones
hydrogen bonding
ion pairs

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201205813

Cite this

@article{d42cdaaf05394df1974f0abb122517ed,

title = "Asymmetric Br{\o}nsted acid catalyzed cycloadditions-efficient enantioselective synthesis of pyrazolidines, pyrazolines, and 1,3-diamines from N-acyl hyrazones and alkenes",

abstract = "A general, metal-free, highly enantioselective Bronsted acid catalyzed [3+2] cycloaddition between hydrazones and alkenes has been developed that affords pyrazolidine derivatives (see scheme). The resulting optically active pyrazolidines can undergo many chemical transformations which allow, for example, the enantioselective synthesis of valuable pyrazolines and 1,3-diamines.",

keywords = "heterocycles, homogeneous catalysis, hydrazones, hydrogen bonding, ion pairs",

author = "Magnus Rueping and Maji, {Modhu Sudan} and K{\"u}{\c c}{\"u}k, {Hatice Ba{\'s}p{\'i}nar} and Iuliana Atodiresei",

year = "2012",

month = dec,

day = "14",

doi = "10.1002/anie.201205813",

language = "English (US)",

volume = "51",

pages = "12864--12868",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley",

number = "51",

}

Asymmetric Brønsted acid catalyzed cycloadditions-efficient enantioselective synthesis of pyrazolidines, pyrazolines, and 1,3-diamines from N-acyl hyrazones and alkenes. / Rueping, Magnus; Maji, Modhu Sudan; Küçük, Hatice Baśpínar et al.
In: Angewandte Chemie - International Edition, Vol. 51, No. 51, 14.12.2012, p. 12864-12868.

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

TY - JOUR

T1 - Asymmetric Brønsted acid catalyzed cycloadditions-efficient enantioselective synthesis of pyrazolidines, pyrazolines, and 1,3-diamines from N-acyl hyrazones and alkenes

AU - Rueping, Magnus

AU - Maji, Modhu Sudan

AU - Küçük, Hatice Baśpínar

AU - Atodiresei, Iuliana

PY - 2012/12/14

Y1 - 2012/12/14

N2 - A general, metal-free, highly enantioselective Bronsted acid catalyzed [3+2] cycloaddition between hydrazones and alkenes has been developed that affords pyrazolidine derivatives (see scheme). The resulting optically active pyrazolidines can undergo many chemical transformations which allow, for example, the enantioselective synthesis of valuable pyrazolines and 1,3-diamines.

AB - A general, metal-free, highly enantioselective Bronsted acid catalyzed [3+2] cycloaddition between hydrazones and alkenes has been developed that affords pyrazolidine derivatives (see scheme). The resulting optically active pyrazolidines can undergo many chemical transformations which allow, for example, the enantioselective synthesis of valuable pyrazolines and 1,3-diamines.

KW - heterocycles

KW - homogeneous catalysis

KW - hydrazones

KW - hydrogen bonding

KW - ion pairs

UR - http://www.scopus.com/inward/record.url?scp=84871003006&partnerID=8YFLogxK

U2 - 10.1002/anie.201205813

DO - 10.1002/anie.201205813

M3 - Article

C2 - 23161809

AN - SCOPUS:84871003006

SN - 1433-7851

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SP - 12864

EP - 12868

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 51

ER -

Asymmetric Brønsted acid catalyzed cycloadditions-efficient enantioselective synthesis of pyrazolidines, pyrazolines, and 1,3-diamines from N-acyl hyrazones and alkenes

Abstract

Keywords

ASJC Scopus subject areas

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