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Synthesis of highly substituted, diastereomerically and enantiomerically pure 3-acyl-tetrahydrofurans from 4-hydroxy-1-alkenyl-carbamates

✍ Scribed by Dieter Hoppe; Thomas Krämer; Cristina Freire Erdbrügger; Ernst Egert

Book ID: 104214050
Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 234 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)72723-7

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✦ Synopsis

The boron trifluoride promoted condensation of 7Z)-anti-4-hvdroxv-1-alkenvl carbamates and aldehvdes (or k&ones) yields the title Compounds with high two;old diastereofacial selectivity. In all, a new flexible strategy is offered for the construction of cis,trans,trans substituted tetrahydrofurans by coupling allyliccarbamates and two (different) aldehydes with only two synthetic steps.

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