[3 + 4] Annulation using a [β-(trimethylsilyl)acryloyl]silane and the lithium enolate of an α,β-unsaturated methyl ketone: (1R,6S,7S)-4-(tert-butyldimethylsiloxy)-6-(trimethylsilyl)bicyclo[5.4.0]undec-4-en-2-one
Organic SynthesesCyclization
![Reaction scheme of [3 + 4] Annulation using a [β-(trimethylsilyl)acryloyl]silane and the lithium enolate of an α,β-unsaturated methyl ketone: (1R,6S,7S)-4-(tert-butyldimethylsiloxy)-6-(trimethylsilyl)bicyclo[5.4.0]undec-4-en-2-one from Organic Syntheses](/orgsyn-image/V76P0199.gif)
A checked procedure from Organic Syntheses, the journal whose preparations are repeated in a second laboratory before publication. The full experimental, with amounts, hazards and characterisation data, is on orgsyn.org.
Reagents
The compound this preparation makes is not in the catalogue, so no reagents or figures are listed here.
More cyclization reactions
- [3+2]-Anionic electrocyclization using 2,3-bis(phenylsulfonyl)-1,3-butadiene: trans-4,7,7-tricarbomethoxy-2-phenylsulfonylbicyclo[3.3.0]oct-1-ene
- (E)-1-Benzyl-3-(1-iodoethylidene)piperidine: nucleophile-promoted alkyne-iminium ion cyclizations
- Conjugate addition–cyclization of a cyanocuprate: 2-carbomethoxy-3-vinylcyclopentanone
- Cyclobutanone via solvolytic cyclization
- Cyclopentadiene annulation via the Skattebøl rearrangement: (1R)-9,9-dimethyltricyclo-[6.1.1.02,6]deca-2,5-diene
- Cyclopentanone annulation via cyclopropanone derivatives: (3aβ,9bβ)-1,2,3a,4,5,9b-hexahydro-9b-hydroxy-3a-methyl-3H-benz[e]inden-3-one