title: Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general approach to (Z)-α-haloacrylates.
abstract: An exceptionally stereoselective and general synthesis of (Z)-α-haloacrylates, ready to undergo various synthetic transformations, has been demonstrated from α-haloacetates and aldehydes in a one-pot manner via the titanium-enolate based asymmetric aldol condensation. Besides being an expedient synthetic procedure, the ready availability of diverse α-haloacetates, exceptional stereoselectivity, and high yields make the process a versatile transformation in organic synthesis. The potential of this method in up-scaling operations has been illustrated.
authors.affiliation: Syngene International Ltd., Biocon Park, Plot Nos. 2 & 3, Bommasandra IV Phase, Jigani Link Road, Bangalore - 560 099, India. john.kallikat@syngeneintl.com john.kallikat@gmail.com.
authors.forename: John Kallikat
authors.initials: JK
authors.lastname: Augustine
authors.forename: Agnes
authors.initials: A
authors.lastname: Bombrun
authors.forename: Srinivasa
authors.initials: S
authors.lastname: Venkatachaliah
authors.forename: Anandh
authors.initials: A
authors.lastname: Jothi
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
chemical_list: D000085:Acetates; D000179:Acrylates; D000447:Aldehydes; D000475:Alkenes; D006846:Hydrocarbons, Halogenated; D014025:Titanium