A convenient method for the synthesis of α-silylacetic acids

Shtelman, Alex V.; Becker, James Y.

doi:10.1016/j.tetlet.2008.03.050

Cited by 9 publications

(5 citation statements)

References 25 publications

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“…According to a procedure reported by Becker et al, 20 to an oven-dried round-bottomed flask (250 mL) equipped with a magnetic stirring bar were added diisopropylamine (24.0 mmol, 1.15 equiv) and anhydrous THF (40 mL). The mixture was cooled to −78 °C, and then n -BuLi 1.6 M (24.0 mmol, 1.15 equiv) was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

Probing Regio- and Enantioselectivity in the Formal [2 + 2] Cycloaddition of C(1)-Alkyl Ammonium Enolates with β- and α,β-Substituted Trifluoromethylenones

et al. 2023

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The isothiourea-catalyzed regio-and enantioselective formal [2 + 2] cycloaddition of C(1)-alkyl and C(1)-unsubstituted ammonium enolates with βand α,β-substituted trifluoromethylenones has been developed. In all cases, preferential [2 + 2]cycloaddition over the alternative [4 + 2]-cycloaddition is observed, giving β-lactones with excellent diastereo-and enantioselectivity (34 examples, up to >95:5 dr, >99:1 er). The regioselectivity of the process was dictated by the nature of the substituents on both reaction components. Solely [2 + 2] cycloaddition products are observed when using α,β-substituted trifluoromethylenones or αtrialkylsilyl acetic acid derivatives; both [2 + 2] and [4 + 2] cycloaddition products are observed when using β-substituted trifluoromethylenones and α-alkyl-α-trialkylsilyl acetic acids as reactants, with the [2 + 2] cycloaddition as the major reaction product. The beneficial role of the α-silyl substituent within the acid component in this protocol has been demonstrated by control experiments.

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Section: Methodsmentioning

confidence: 99%

Probing Regio- and Enantioselectivity in the Formal [2 + 2] Cycloaddition of C(1)-Alkyl Ammonium Enolates with β- and α,β-Substituted Trifluoromethylenones

et al. 2023

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“…Me 3 GeCH 2 COOH [2À(trimethylgermyl)acetic acid, (I)] was prepared according to the procedure previously described for the synthesis of a-silylcarboxylic acids [6,7]. In a typical example for the synthesis of 2À(trimethylgermyl)acetic acid (I), diisopropylamine (10.7 mmol, 1.63 ml) and anhydrous tetrahydrofuran (30 ml) were added to an oven dried round-bottomed flask (100 ml) equipped with a magnetic stirring bar.…”

Section: Synthetic Procedures Of A-germyl and A-silylcarboxylic Acidsmentioning

confidence: 99%

“…An efficient synthesis of a-silylacetic acids with various substituents attached to the silicon atom (R 0 R 00 R 000 SiCH 2 COOH), as well as of a-silylcarboxylic acids with various alkyl groups at the aposition [R 0 R 00 R 000 SiCH(R)COOH] has been described previously [6,7].…”

Section: Introductionmentioning

confidence: 99%