title: The stereochemical outcome of allyl magnesium and indium additions to 5-substituted norbornen-7-ones and its application to cis fused carbocycle formation via ring rearrangement metathesis.
abstract: The addition of allyl magnesium and allyl indium reagents to a key TBS protected norbornenyl building block, synthesised in 6-steps from commercially available 1,1-dimethoxy-2,3,4,5-tetrachlorocyclopentadiene, has been achieved providing the syn addition products with high diastereoselectivity. The subsequent exposure of the addition products to metathesis conditions, in the presence of ethene, then provided cis fused[3.0.3]-carbocycles with very high regioselectivity, via a Ring Rearrangement Metathesis (RRM) transformation.
authors.affiliation: Department of Chemistry, Loughborough University, Leicestershire, LE11 3TU, UK.
authors.forename: Patricia E
authors.initials: PE
authors.lastname: Standen
authors.forename: Dharati
authors.initials: D
authors.lastname: Dodia
authors.forename: Mark R J
authors.initials: MR
authors.lastname: Elsegood
authors.forename: Simon J
authors.initials: SJ
authors.lastname: Teat
authors.forename: Marc C
authors.initials: MC
authors.lastname: Kimber
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D003500:Cyclization; D007204:Indium / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000498:Allyl Compounds; D009636:Norbornanes; D007204:Indium; D008274:Magnesium