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Temperature- and Reagent-Controlled Complementary Syn- and Anti-Selective Enolboration-Aldolization of Substituted Phenylacetates

Angela Y. Thomas, Tommy L. Walls III, Brionna N. Nelson, Stafford W. Primeaux and Prem B. Chanda*

*Department of Chemistry and Physics, Southeastern Louisiana University, Hammond, Louisiana 70402, United States, Email:

A. Y. Thomas, T. L. Walls III, B. N. Nelson, S. W. Primeaux, P. B. Chanda, J. Org. Chem., 2021, 86, 6184-6194.

DOI: 10.1021/acs.joc.0c03024

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Whereas a dicyclohexylboron triflate/triethylamine (Cy2BOTf/Et3N)-mediated enolboration-aldolization reaction of methyl arylacetates provides anti-aldols at low temperatures, a combination of a less bulky boron reagent (dibutylboron triflate, Bu2BOTf), a bulky amine (iPr2NEt), and ambient temperature is required to obtain syn-aldols.

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Solvent- or Temperature-Controlled Diastereoselective Aldol Reaction of Methyl Phenylacetate

P. V. Ramachandran, P. B. Chanda, Org. Lett., 2012, 14, 4346-4349.

Key Words

β-hydroxy esters

ID: J42-Y2021