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Enantiomerically Pure Vinylcyclopropylboronic Esters

✍ Scribed by Erwin Hohn; Jiří Paleček; Jörg Pietruszka; Wolfgang Frey

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
721 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Vinylcyclopropanes are versatile intermediates and products in organic synthesis. The corresponding enantiomerically pure boronic esters should lead to highly flexible building blocks with a variety of applications. A detailed study towards the selective synthesis of (E)‐ and (Z)‐vinyl derivatives starting from the known diastereo‐ and enantiopure cyclopropylmethanols 3 and 4 is presented. The boronic esters were activated via their trifluoroboronates; the optimization of the reaction is discussed. The endeavour culminated in the synthesis of (–)‐(1__S__,2__S__)‐dictyopterene A (38). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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