Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 11, Pages 4368-4371Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo900477q
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Funding
- The National Science Foundation [0750463]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0750463] Funding Source: National Science Foundation
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We present an efficient synthesis of beta-hydroxyesters and alpha,beta-unsaturated esters via activation of the silicon-carbon bond of alpha-trimethylsilylethyl acetate using catalytic amounts of the commercially available P(i-PrNCH2CH2)(3)N 1a. Selectivity for either of these two products can be achieved simply by altering the catalyst loading and reaction temperature to afford addition or stereoselective condensation. This method is mild and tolerates a wide array of functional groups.
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