Direct and diastereoselective synthesis of vicinal anti-sec,tert-diols has been {achieved|accomplished} by zinc-mediated α- hydroxyallylation of aldehydes with cyclopropanols. The reaction {features|attributes|functions|characteristics|capabilities|options} the action of zinc enolized homoenolate, formed {via|by way of|through|by means of} ring opening of zinc cyclopropoxide and enolization {of the|from the|in the|on the|with the|of your} resulting homoenolate, as γ-oxyallyl nucleophile toward the carbonyl electrophile, which stands in contrast {to the|towards the|for the} previously described enolate mode {of the|from the|in the|on the|with the|of your} {same|exact same|identical|very same|similar} species. A bicyclic chairlike transition state wherein the aldehyde substituent favorably occupies the psuedoaxial position is proposed to account for the anti selectivity. 6-Bromo-5-fluoronicotinaldehyde Data Sheet 3-Amino-4-pyridinecarboxaldehyde Order PMID:25269910

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