Enantiomerically Pure Vinylcyclopropylboronic Esters

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 s...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2009-08, Vol.2009 (22), p.3765-3782
Main Authors: Hohn, Erwin, Paleček, Jiří, Pietruszka, Jörg, Frey, Wolfgang
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Asymmetric synthesis
Boron
Chemistry
Cyclopropane
Exact sciences and technology
Natural products
Organic chemistry
Palladium
Preparations and properties
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Summary: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 (–)‐(1S,2S)‐dictyopterene A (38). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) Isomerically pure vinylcyclopropanes (e.g., 10) have been prepared from cyclopropylboronic esters (e.g., 3). A number of alternative procedures for their synthesis via the corresponding alkyltrifluoroborateshave been established and they require relatively mild reaction conditions for their activation. The sequence has been applied to the synthesis of natural dictypterene A (38).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200900414