title: Co(III)(salen)-catalyzed phenolic kinetic resolution of two stereocentered benzyloxy and azido epoxides: its application in the synthesis of ICI-118,551, an anti-hypertensive agent.
abstract: The salen Co(III)-catalyzed phenolic kinetic resolution of racemic anti- or syn-azido and benzyloxy epoxides provides a practical route to a range of enantioenriched anti- or syn-1-aryloxy-3-azido or benzyloxy-2-alcohols in excellent yields and ees. The synthetic potential of this protocol is illustrated with an enantioselective synthesis of ICI-118,551, a β-blocker, in a highly optically pure form (99% ee).
authors.affiliation: Chemical Engineering and Process Development Division, National Chemical Laboratory, Dr Homi Bhabha Road, Pune 411008, India. a.sudalai@ncl.res.in.
authors.forename: Pratibha U
authors.initials: PU
authors.lastname: Karabal
authors.forename: Dayanand A
authors.initials: DA
authors.lastname: Kamble
authors.forename: Arumugam
authors.initials: A
authors.lastname: Sudalai
mesh_terms: D000959:Antihypertensive Agents / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003035:Cobalt / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry*; D007700:Kinetics; D009942:Organometallic Compounds / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D011412:Propanolamines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000959:Antihypertensive Agents; D004852:Epoxy Compounds; D005029:Ethylenediamines; D009942:Organometallic Compounds; D010636:Phenols; D011412:Propanolamines; D003035:Cobalt; C026777:ICI 118551; C011452:disalicylaldehyde ethylenediamine