焦谷氨酸衍生物的对映选择性迈克尔质子转移内酰胺化:二甲基-(S,E)-5-氧-3-苯乙烯-1-酰基吡咯烷-2,2-二羧酸酯的合成。

IF 0.7 Q4 CHEMISTRY, ORGANIC

Organic Syntheses Pub Date : 2021-01-01 DOI:10.15227/orgsyn.098.0194

Christian M Chaheine, Conner J Song, Paul T Gladen, Daniel Romo

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Enantioselective Michael-Proton Transfer-Lactamization for Pyroglutamic Acid Derivatives: Synthesis of Dimethyl-(S,E)-5-oxo-3-styryl-1-tosylpyrrolidine-2,2-dicarboxylate.

A. Dimethyl 2-amino((4-methylphenyl)sulfonamido)malonate (2). To a single-necked, 500 mL round-bottomed flask containing a football-shaped, teflon-coated stir bar (5 cm) and fitted with a 24/40 glass, threaded gas-inlet adapter with a silicone/PTFE septa (Figure 1A) (Note 2), in-turn connected via chemically resistant tubing to a vacuum/nitrogen manifold is added commercially available dimethyl aminomalonate hydrochloride (1, 12.5 g, MeO2C CO2Me NH2 •HCl Ts2O, NEt3 THF, 0 to 23 °C MeO2C CO2Me NHTs

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Organic Syntheses Chemistry-Organic Chemistry

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1.20

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