Cyclodextrin mediated solvent-free enantioselective photocyclization of N-alkyl pyridones

J. Shailaja; S. Karthikeyan; V. Ramamurthy

doi:10.1016/S0040-4039(02)02338-9

Cyclodextrin mediated solvent-free enantioselective photocyclization of N-alkyl pyridones

J. Shailaja, S. Karthikeyan, V. Ramamurthy

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

44 Scopus citations

Abstract

Irradiation of N-methyl pyridone and N-ethyl pyridone included in β-cyclodextrin yields the photocylized product, chiral 2-azabicyclo[2.2.0]-hex-5-en-3-ones, in ∼60% enantiomeric excess. The inclusion complex is readily made by mechanically mixing the host β-cyclodextrin and the guest pyridone.

Original language	English (US)
Pages (from-to)	9335-9339
Number of pages	5
Journal	Tetrahedron Letters
Volume	43
Issue number	51
DOIs	https://doi.org/10.1016/S0040-4039(02)02338-9
State	Published - Dec 16 2002
Externally published	Yes

Keywords

Chiral induction
Cyclodextrin
Inclusion complex
Pyridone

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/S0040-4039(02)02338-9

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title = "Cyclodextrin mediated solvent-free enantioselective photocyclization of N-alkyl pyridones",

abstract = "Irradiation of N-methyl pyridone and N-ethyl pyridone included in β-cyclodextrin yields the photocylized product, chiral 2-azabicyclo[2.2.0]-hex-5-en-3-ones, in ∼60% enantiomeric excess. The inclusion complex is readily made by mechanically mixing the host β-cyclodextrin and the guest pyridone.",

keywords = "Chiral induction, Cyclodextrin, Inclusion complex, Pyridone",

author = "J. Shailaja and S. Karthikeyan and V. Ramamurthy",

note = "Funding Information: The authors thank the National Science Foundation for support of the research (CHE-9904187 and CHE-0212042), T. Bach and H. Bergmann for providing useful information about the chiral separation of the photoproducts, A. Pradhan for help with the solid state NMR spectra and J. Sivaguru for reproducing the key results presented in this letter. ",

year = "2002",

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doi = "10.1016/S0040-4039(02)02338-9",

language = "English (US)",

volume = "43",

pages = "9335--9339",

journal = "Tetrahedron Letters",

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publisher = "Elsevier Limited",

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TY - JOUR

T1 - Cyclodextrin mediated solvent-free enantioselective photocyclization of N-alkyl pyridones

AU - Shailaja, J.

AU - Karthikeyan, S.

AU - Ramamurthy, V.

N1 - Funding Information: The authors thank the National Science Foundation for support of the research (CHE-9904187 and CHE-0212042), T. Bach and H. Bergmann for providing useful information about the chiral separation of the photoproducts, A. Pradhan for help with the solid state NMR spectra and J. Sivaguru for reproducing the key results presented in this letter.

PY - 2002/12/16

Y1 - 2002/12/16

N2 - Irradiation of N-methyl pyridone and N-ethyl pyridone included in β-cyclodextrin yields the photocylized product, chiral 2-azabicyclo[2.2.0]-hex-5-en-3-ones, in ∼60% enantiomeric excess. The inclusion complex is readily made by mechanically mixing the host β-cyclodextrin and the guest pyridone.

AB - Irradiation of N-methyl pyridone and N-ethyl pyridone included in β-cyclodextrin yields the photocylized product, chiral 2-azabicyclo[2.2.0]-hex-5-en-3-ones, in ∼60% enantiomeric excess. The inclusion complex is readily made by mechanically mixing the host β-cyclodextrin and the guest pyridone.

KW - Chiral induction

KW - Cyclodextrin

KW - Inclusion complex

KW - Pyridone

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U2 - 10.1016/S0040-4039(02)02338-9

DO - 10.1016/S0040-4039(02)02338-9

M3 - Article

AN - SCOPUS:0037121566

VL - 43

SP - 9335

EP - 9339

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 51

ER -

Cyclodextrin mediated solvent-free enantioselective photocyclization of N-alkyl pyridones

Abstract

Keywords

ASJC Scopus subject areas

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