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Powerful Kinetic Diastereoselection in Ruthenium-Catalysed Ring-Closing Metathesis of (Homoallyl)vinylcyclopropanes

✍ Scribed by Guy C. Lloyd-Jones; Martin Murray; Rosie A. Stentiford; Paul A. Worthington

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
553 KB
Volume
2000
Category
Article
ISSN
1434-193X

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✦ Synopsis

Homoallyl-substituted vinyl cyclopropanes 1a-c, which are readily prepared by reaction of allylindium reagents with α,β-unsaturated ketones and aldehydes, undergo Ru-catalysed RCM reactions with Grubbs catalyst to give [4.1.0]bicyclooct-2-ene (norcarene) type bicyclic products. Noncyclisable 'trans' homoallyl-substituted vinyl cyclopropanes 1b and 1c are separated from their 'cis' diastereomers by RCM to 5b and 5c -but only with moderate efficiency due to a competing homo-cross metathesis ('dimerisation') to give 7b and 7c, respectively. However, the four diastereomers of the (homoallyl)distyrylcyclopropane 14a obtained from indium-

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ChemInform Abstract: Powerful Kinetic Di
ChemInform Abstract: Powerful Kinetic Diastereoselection in Ruthenium-Catalyzed Ring-Closing Metathesis of (Homoallyl)vinylcyclopropanes.
✍ Guy C. Lloyd-Jones; Martin Murray; Rosie A. Stentiford; Paul A. Worthington 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 29 KB 👁 1 views

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