High stereoselectivity in one-pot intramolecular cycloadditions of olefinic silyl nitronates

Authors
Cheng, Q Oritani, T Horiguchi, T Shi, QW
Citation
Q. Cheng et al., High stereoselectivity in one-pot intramolecular cycloadditions of olefinic silyl nitronates, EUR J ORG C, (10), 1999, pp. 2689-2693
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
10
Year of publication
1999
Pages
2689 - 2693
Database
ISI
SICI code
1434-193X(199910):10<2689:HSIOIC>2.0.ZU;2-W
Abstract
Intramolecular silyl nitronate olefin cycloaddition starting from nitro ole fins 1 and leading to substituted tetrahydrofuran rings fused to isoxazolin es 5 has been achieved in a one-pot protocol involving Michael addition, si lylation, cycloaddition, and desilylation steps. The results show that unli ke nitrile oxides, silyl nitronates undergo highly stereoselective intramol ecular cycloadditions to produce functionalized heterocyclic rings.