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

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journal contribution
posted on 09.04.2021, 19:37 by Angela Y. Thomas, Tommy L. Walls III, Brionna N. Nelson, Stafford W. Primeaux, Prem B. Chanda
In contrast to methyl phenylacetates, methyl arylacetates do not provide syn-aldols in the dicyclohexylboron triflate/triethylamine (Chx2BOTf/Et3N)-mediated enolboration–aldolization reaction. However, a combination of a less bulky boron reagent (dibutylboron triflate, n-Bu2BOTf), a bulky amine (i-Pr2NEt), and ambient temperature is required to obtain syn-aldols from methyl arylacetates. The corresponding anti-aldol products have been synthesized by the enolboration–aldolization of methyl arylacetates in the presence of Chx2BOTf/Et3N at a lower temperature. We report the first example of a complementary syn- and anti-selective enolboration–aldolization of arylacetates.