Diastereo- and enantioselective boron-mediated aldol reaction of Phenylacetates
Abstract
Reported herein is the diastereo- and enantioselective aldol reaction of Phenylacetates. Synthesis of racemic methyl anti- or syn-β-hydroxy-α-phenylacetates is accomplished by simply changing the enolization-aldolization temperature. The effects of solvent, temperature, amine, alkoxy group of ester, and reagent bulk on diastereoselectivity for enolboration-aldolization of phenylacetate is discussed. The first application of less bulky reagent, di-n-butylboron triflate, for the anti-selective aldol reaction of esters is described. Diisopinocampheylboron triflate-mediated enantioselective syn- and anti - aldol reaction of phenylacetate is also discussed. The application of double diastereoselective anti-aldol reaction of phenylacetate for the synthesis of C1-C9 subunit of 6-phenyl-6-desmethyl dictyostatin is also described.
Degree
Ph.D.
Advisors
Ramachandran, Purdue University.
Subject Area
Chemistry|Organic chemistry
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