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A general chemoenzymatic synthesis of enenatiopures cis beta-amino alcohols from microbially derived cis-glycols
Enantiomerically pure cis-glycols, derived through the microbial metabolism of hydrocarbons, represent a valuable chiral pool for the synthesis of cis beta-amino alcohols. One generally applicable route to these important chiral intermediates is described. Reaction of the metabolically formed diol with alpha-acetoxyisobutyryl chloride affords regio- and stereoselectively a single trans-1,2-chlorohydrin acetate isomer. Displacement of chloride by azide, aminolysis of the ester and reduction of the azide provides the requisite amino alcohols. This 4-step route is highly efficient and affords the cis beta-amino alcohol enantiomers in 41-57% overall yields. Using the highly enantiopure amino alcohols diastereomeric oxazaborolidines were prepared with both (-)-(S)- and (+)-(R)-[2-(1-methoxyethyl)phenyl]boronic acids. As described herein, these derivatives are potentially useful for absolute configurational assignments to cis amino alcohols.
Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.name: (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol, you can also check out more blogs about126456-43-7
Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis