Organic Letters 2013-06-21

A practical method for the synthesis of highly enantioenriched trans-1,2-amino alcohols.

James A Birrell, Eric N Jacobsen

Index: Org. Lett. 15(12) , 2895-7, (2013)

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Abstract

A highly enantioselective addition of phenyl carbamate to meso-epoxides has been developed to efficiently generate protected trans-1,2-amino alcohols. This transformation is promoted by an oligomeric (salen)Co-OTf catalyst and has been used to prepare two useful 2-aminocycloalkanol hydrochlorides in enantiopure form on a multigram scale from commercially available starting materials.