Stereoselective synthesis of substituted tetrahydrofurans - identification and analysis by proton NMR and MNDO, MM2 calculations

P. Tarakeshwar; Javed Iqbal; S. Manogaran

doi:10.1016/S0040-4020(01)80924-8

Stereoselective synthesis of substituted tetrahydrofurans - identification and analysis by proton NMR and MNDO, MM2 calculations

P. Tarakeshwar
, Javed Iqbal
, S. Manogaran

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

14 Scopus citations

Abstract

Methyl acetoacetate and terminal olefins react in the presence of cobalt(II) acetate and oxygen to give 5-alkyl-2-hydroxy-2-methyl-3-methoxycarbonyl tetrahydrofurans in a highly stereoselective manner. Proton NMR, semiempirical MNDO and empirical MM2 methods are used to identify the particular diastereomer and the energetics of the different isomers are discussed.

Original language	English (US)
Pages (from-to)	297-304
Number of pages	8
Journal	Tetrahedron
Volume	47
Issue number	2
DOIs	https://doi.org/10.1016/S0040-4020(01)80924-8
State	Published - Jan 1991
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)80924-8

Cite this

@article{744e59109fdc40e9a13a7b5a00091c68,

title = "Stereoselective synthesis of substituted tetrahydrofurans - identification and analysis by proton NMR and MNDO, MM2 calculations",

abstract = "Methyl acetoacetate and terminal olefins react in the presence of cobalt(II) acetate and oxygen to give 5-alkyl-2-hydroxy-2-methyl-3-methoxycarbonyl tetrahydrofurans in a highly stereoselective manner. Proton NMR, semiempirical MNDO and empirical MM2 methods are used to identify the particular diastereomer and the energetics of the different isomers are discussed.",

author = "P. Tarakeshwar and Javed Iqbal and S. Manogaran",

note = "Funding Information: MM2 performs better in predicting the relative energies and distances in this molecule as expected and 1s In agreement with the proton NMR results. In structure 3 the HX and the CH3 proton distance (3 IO-4.37 MM2/3.22-4 56 MNDO) at C-2 fits well with the observed NOESY cross peak (CH3, HX) as compared to structure 2 (4.44-4.86 MM2/4.61-5 21 MNDO) Thus, the energetlcs and proton NMR spectra clearly indicate 2 as the most favoured isomer Acknowledgements . We thank Council of Sclentlfic and Industrial Research, New Delhi, for providing the financial assistance and Bangalore NMR faclllty for recording the spectra.",

year = "1991",

month = jan,

doi = "10.1016/S0040-4020(01)80924-8",

language = "English (US)",

volume = "47",

pages = "297--304",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "2",

}

TY - JOUR

T1 - Stereoselective synthesis of substituted tetrahydrofurans - identification and analysis by proton NMR and MNDO, MM2 calculations

AU - Tarakeshwar, P.

AU - Iqbal, Javed

AU - Manogaran, S.

N1 - Funding Information: MM2 performs better in predicting the relative energies and distances in this molecule as expected and 1s In agreement with the proton NMR results. In structure 3 the HX and the CH3 proton distance (3 IO-4.37 MM2/3.22-4 56 MNDO) at C-2 fits well with the observed NOESY cross peak (CH3, HX) as compared to structure 2 (4.44-4.86 MM2/4.61-5 21 MNDO) Thus, the energetlcs and proton NMR spectra clearly indicate 2 as the most favoured isomer Acknowledgements . We thank Council of Sclentlfic and Industrial Research, New Delhi, for providing the financial assistance and Bangalore NMR faclllty for recording the spectra.

PY - 1991/1

Y1 - 1991/1

N2 - Methyl acetoacetate and terminal olefins react in the presence of cobalt(II) acetate and oxygen to give 5-alkyl-2-hydroxy-2-methyl-3-methoxycarbonyl tetrahydrofurans in a highly stereoselective manner. Proton NMR, semiempirical MNDO and empirical MM2 methods are used to identify the particular diastereomer and the energetics of the different isomers are discussed.

AB - Methyl acetoacetate and terminal olefins react in the presence of cobalt(II) acetate and oxygen to give 5-alkyl-2-hydroxy-2-methyl-3-methoxycarbonyl tetrahydrofurans in a highly stereoselective manner. Proton NMR, semiempirical MNDO and empirical MM2 methods are used to identify the particular diastereomer and the energetics of the different isomers are discussed.

UR - https://www.scopus.com/pages/publications/0025966464

UR - https://www.scopus.com/pages/publications/0025966464#tab=citedBy

U2 - 10.1016/S0040-4020(01)80924-8

DO - 10.1016/S0040-4020(01)80924-8

M3 - Article

AN - SCOPUS:0025966464

SN - 0040-4020

VL - 47

SP - 297

EP - 304

JO - Tetrahedron

JF - Tetrahedron

IS - 2

ER -

Stereoselective synthesis of substituted tetrahydrofurans - identification and analysis by proton NMR and MNDO, MM2 calculations

Abstract

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