Synthetic Communications

An International Journal for Rapid Communication of Synthetic Organic Chemistry

Volume 40, 2009 - Issue 1

203

Views

CrossRef citations to date

Altmetric

Original Articles

Stereoselective Synthesis of Substituted 3a-Hydroxy Diquinanones and 3a-Hydroxy Hydrindanones via Intramolecular Cycloaddition of Nitrile Oxides

Anne-Sophie Chapelon Laboratoire de Synthèse Organique, Equipe Chirosciences, CNRS 6263, Marseille, France

Michel Giorgi Spectropôle, Université d'Aix-Marseille, Faculté des Sciences de St-Jérôme, Marseille, France

Cyril Ollivier Laboratoire de Synthèse Organique, Equipe Chirosciences, CNRS 6263, Marseille, FranceCorrespondence[email protected]

Maurice Santelli Laboratoire de Synthèse Organique, Equipe Chirosciences, CNRS 6263, Marseille, France

Abstract

trans-1,3-Divinylcyclopentanes bearing a ω-nitroalkyl chain (C₂ or C₃) in the 2-position were submitted to an intramolecular nitrile oxide cycloaddition process to give tricyclic isoxazoline precursors of 4-hydroxymethylbicyclo[3.3.0]octan-1-ol-3-ones or 5-hydroxymethyl-9-vinylbicyclo[4.3.0]nonan-1-ol-4-ones.

Keywords:

ACKNOWLEDGMENTS

A.-S. C. is grateful to the CNRS and la Région PACA for grants. We are indebted to Dr. B. Vacher (Pierre Fabre Médicaments, Castres, France) for helpful comments. This work has been financially supported by the CNRS and the Ministère de l'Education Nationale.

Notes

^aB3LYP/6-311G++(p, d) level of the theory.

^bB3LYP/6-311G++(2df, 2pd) level of the theory.

^cWithout ZPE correction.

^aw = 1/[σ ²(Fo²) + (0.1205P)² + 0.091P] where P = (Fo² + 2Fc²)/3.

^bw = 1/[σ ²(Fo²) + (0.0208P)² + 1.1795P] where P = (Fo² + 2Fc²)/3.

^cw = 1/[σ ²(Fo²) + (0.1007P)² + 2.9671P] where P = (Fo² + 2Fc²)/3.

^dw = 1/[σ Citation ² (FoCitation ² ) + (0.0909P)Citation ² +0.1063P] where P = (Fo² + 2Fc²)/3.

Intramolecular cycloaddition of nitrile oxide generated from oxime (Kozikowski method): (a) Ghosh , A. K. ; Gong , G. Org. Lett. 2007 , 9 , 1437 – 1440 ; (b) Noguchi , M. ; Tsukimoto , A. ; Kadowaki , A. ; Hikata , J. ; Kakehi , A. Tetrahedron Lett. 2007 , 48 , 3539 – 3542 ; (c) Nath , M. ; Mukhopadhyay , R. ; Bhattacharjya , A. Org. Lett. 2006 , 8 , 317 – 320 ; (d) Yokoshima , S. ; Ueda , T. ; Kobayashi , S. ; Sato , A. ; Kuboyama , T. ; Tokuyama , H. ; Fukuyama , T. J. Am. Chem. Soc. 2002 , 124 , 2137 – 2139 ; (e) Aungst , R. A. Jr. ; Chan , C. ; Funk , R. L. Org. Lett. 2001 , 3 , 2611 – 2613 ; (f) Falb , E. ; Nudelman , A. ; Gottlieb , H. E. ; Hassner , A. Eur. J. Org. Chem. 2000 , 645 – 655 ; (g) Doi , T. ; Hijikuro , I. ; Takahashi , T. J. Am. Chem. Soc. 1999 , 121 , 6749 – 6750 ; (h) Sato , H. ; Kim , Y. S. ; Shibasaki , M. Tetrahedron Lett. 1999 , 40 , 2973 – 2976 ; (i) Takahashi , T. ; Hirose , Y. ; Iwamoto , H. ; Doi , T. J. Org. Chem. 1998 , 63 , 5742 – 5743 ; (j) Hirai , Y. ; Nagaoka , H. Tetrahedron Lett. 1997 , 38 , 1969 – 1970 ; (k) Takahashi , T. ; Iwamoto , H. Tetrahedron Lett. 1997 , 38 , 2483 – 2486 ; (l) Jung , M. E. ; Vu , B. T. Tetrahedron Lett. 1996 , 37 , 451 – 454 ; (m) Takahashi , T. ; Nakazawa , M. ; Sakamoto , Y. ; Houk , K. N. Tetrahedron Lett. 1993 , 34 , 4075 – 4078 ; (n) Ihara , M. ; Tokunaga , Y. ; Fukumoto , K. J. Org. Chem. 1990 , 55 , 4497 – 4498 ; (o) Hassner , A. ; Murthy , K. S. K. ; Padwa , A. ; Chiacchio , U. ; Dean , D. C. ; Shoffstall , A. M. J. Org. Chem. 1989 , 54 , 5277 – 5286 ; (p) Okamoto , S. ; Kobayashi , Y. ; Kato , H. ; Hori , K. ; Takahashi , T. ; Tsuji , J. ; Sato , F. J. Org. Chem. 1988 , 53 , 5590 – 5592 ; (q) Annunziata , R. ; Cinquini , M. ; Cozzi , F. ; Genari , C. ; Raimondi , L. J. Org. Chem. 1987 , 52 , 4674 – 4681 ; (r) Kozikowski , A. P. ; Stein , P. D. J. Org. Chem. 1984 , 49 , 2301 – 2309 .

PubMed Web of Science ®Google Scholar

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Stereoselective Synthesis of Substituted 3a-Hydroxy Diquinanones and 3a-Hydroxy Hydrindanones via Intramolecular Cycloaddition of Nitrile Oxides

Information for

Open access

Opportunities

Help and information

Stereoselective Synthesis of Substituted 3a-Hydroxy Diquinanones and 3a-Hydroxy Hydrindanones via Intramolecular Cycloaddition of Nitrile Oxides

Abstract

ACKNOWLEDGMENTS

Notes

Reprints and Corporate Permissions

Academic Permissions

Related research

To cite this article:

Download citation

Information for

Open access

Opportunities

Help and information

Keep up to date

Your download is now in progress and you may close this window

Login or register to access this feature