title: Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols.
abstract: A novel synthetic strategy toward the asymmetric synthesis of vicinal diols bearing a tertiary center is presented. The method encompasses the dinuclear Mg-catalyzed asymmetric addition of ethyl diazoacetate into several aldehydes, oxidation of the diazo functionality, and diastereoselective alkyl transfer of various organometallics into the resulting chiral β-hydroxy-α-ketoesters to afford a diverse range of 1,2-diols in high yield, diastereoselectivity, and chirality transfer.
authors.affiliation: Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Sushant
authors.initials: S
authors.lastname: Malhotra
authors.forename: Philipp
authors.initials: P
authors.lastname: Koschker
authors.forename: Pascal
authors.initials: P
authors.lastname: Ellerbrock
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D003979:Diazonium Compounds; C032111:diazoacetic ester
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