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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 8
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Original Articles

Regioselectivity and Stereoselectivity in the Intramolecular Nitrile Oxide-Olefin Cycloaddition (INOC) Reaction and the Intramolecular Silyl Nitronate-Olefin Cycloaddition (ISOC) Reaction

Hyoung Rae Kim Korea Research Institute of Chemical Technology, P. O. Box 9, Daedeog-Danji, Daejeon, 305-606, Korea
,
Kyoung Mahn Kim Korea Research Institute of Chemical Technology, P. O. Box 9, Daedeog-Danji, Daejeon, 305-606, Korea
,
Jae Nyoung Kim Korea Research Institute of Chemical Technology, P. O. Box 9, Daedeog-Danji, Daejeon, 305-606, Korea
&
Eung K. Ryu Korea Research Institute of Chemical Technology, P. O. Box 9, Daedeog-Danji, Daejeon, 305-606, Korea
Pages 1107-1116 | Received 24 Sep 1993, Published online: 23 Sep 2006
 
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Abstract

Both INOC and ISOC reactions of 1 which has two different double bonds in a molecule (allylic and homoallylic double bond) showed high regioselectivity for allylic double bond to make [5,5] ring system. INOC reactions of 1 and 6 showed high diastereoselectivity for 4-substituents, whereas ISOC reaction did for 6-substituents of tetrahydrofuroisoxazolines.

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