title: Synthesis of spirocycles via ring closing metathesis of heterocycles carrying gem-diallyl substituents obtained via ring opening of (halomethyl)cyclopropanes with allyltributyltin.
abstract: In the presence of allyl tri-n-butyltin--AIBN, cyclopropylmethyl bromides/xanthates undergo ring-opening reaction with concomitant formation of geminal diallyl derivatives in good yields. The ring closing metathesis reactions on geminal diallyl derivatives with Grubbs' catalyst provided spirocyclopentenyl products. Combination of these two methodologies has been applied to the synthesis of mono-, bis-cyclopentyl-carbohydrates as well as spirocyclopentylproline derivatives.
authors.affiliation: National Chemical Laboratory, Pune, 411 008, India.
authors.forename: Mukund K
authors.initials: MK
authors.lastname: Gurjar
authors.forename: Somu V
authors.initials: SV
authors.lastname: Ravindranadh
authors.forename: Kuppusamy
authors.initials: K
authors.lastname: Sankar
authors.forename: Sukhen
authors.initials: S
authors.lastname: Karmakar
authors.forename: Joseph
authors.initials: J
authors.lastname: Cherian
authors.forename: Mukund S
authors.initials: MS
authors.lastname: Chorghade
mesh_terms: D003521:Cyclopropanes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013057:Spectrum Analysis; D014220:Trialkyltin Compounds / Q000737:chemistry*
chemical_list: D003521:Cyclopropanes; D006571:Heterocyclic Compounds; D014220:Trialkyltin Compounds; C011559:tributyltin