title: Diastereoselective zinco-cyclopropanation of chiral allylic alcohols with gem-dizinc carbenoids.
abstract: The highly diastereoselective zinco-cyclopropanation of chiral allylic alcohols using gem-dizinc carbenoids is described. The reaction produces three contiguous stereogenic centers, and the resulting chiral cyclopropylzinc derivatives can be trapped with electrophiles with retention of configuration. Simple functional group manipulations lead to the efficient synthesis of orthogonally protected 1,2,3-substituted cyclopropane derivatives.
authors.affiliation: Département de Chimie, Université de Montréal, Montréal, Québec, Canada H3C 3J7.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Fournier
authors.forename: Simon
authors.initials: S
authors.lastname: Mathieu
authors.forename: André B
authors.initials: AB
authors.lastname: Charette
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D003521:Cyclopropanes; D009942:Organometallic Compounds; D020005:Propanols; C006463:allyl alcohol; D015032:Zinc