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ChemInform Abstract: Regiochemical Control of the Ring-Opening of Epoxides by Means of Chelating Processes. Part 13. Synthesis and Ring-Opening Reactions of the Diastereoisomeric cis- and trans-Epoxides Derived from 3-(Benzyloxy)cyclopentene and 2-(Benzyloxy)-2,5-dihydrofuran.

✍ Scribed by P. CROTTI; V. DI BUSSOLO; L. FAVERO; F. MACCHIA; M. PINESCHI

Publisher: John Wiley and Sons
Year: 2010
Weight: 39 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199848096

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✦ Synopsis

Regiochemical Control of the Ring-Opening of Epoxides by Means of Chelating Processes. Part 13. Synthesis and Ring-Opening Reactions of the Diastereoisomeric cis-and trans-Epoxides Derived from 3-(Benzyloxy)cyclopentene and 2-(Benzyloxy)-2,5-dihydrofuran.

-Under standard conditions the cis-epoxides (II) and (IX) yield predominantly the C-1 ring-opening products. Under chelating conditions unexpected increase in C-2 selectivity is observed. The trans-epoxides (II) and (X) exclusively yield C-1 ring-opening products under both conditions. -(CROTTI, P.; DI

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