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. 2023 Feb 17:116:154334.
doi: 10.1016/j.tetlet.2022.154334. Epub 2022 Dec 28.

Preparation of β-Hydroxyketones (Aldols) from the Alkylation of O-Silyl Aryl Cyanohydrins with Epoxides

Lissa D Gilreath  1 , Diamond R Melendez  1 , Caylie A McGlade  1 , Jennifer E Shoemaker  2 , Dakoda W Mullinax  1 , Aaron M Hartel  1
Affiliations

Preparation of β-Hydroxyketones (Aldols) from the Alkylation of O-Silyl Aryl Cyanohydrins with Epoxides

Lissa D Gilreath et al. Tetrahedron Lett. .

Abstract

β-Hydroxyketones (aldols) are prepared from the alkylation-deprotection of O-silylated aryl cyanohydrins with epoxides. Key to the success of the method was the suppression of an in situ cyclic imidate formation that occurs upon initial opening of the epoxide ring.

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Figures

Scheme 1.
Scheme 1.
Aldols from acyl anion equivalents.
Scheme 2.
Scheme 2.
Formation of aldols via the reaction of protected cyanohydrin anions with epoxides.
Scheme 3.
Scheme 3.
Formation of desired adduct and cyclic imidate.
Scheme 4.
Scheme 4.
Equilibrium of adduct and imidate via their conjugate bases during acid quench.
Scheme 5.
Scheme 5.
Successful formation of aldol using after deprotection with TBAF.
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References

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