Organic Process Research & Development
Organic Process Research & Development
2 years ago

[ASAP] Asymmetric Synthesis of Optically Active 3‑Cyclohexene-1-carboxylic Acid Utilizing Lactic Ester as a Chiral Auxiliary in the Diastereoselective Diels–Alder Reaction

[ASAP] Asymmetric Synthesis of Optically Active 3‑Cyclohexene-1-carboxylic Acid Utilizing Lactic Ester as a Chiral Auxiliary in the Diastereoselective Diels–Alder Reaction
Hidenori Ochiai, Wakana Hayashi, Akira Nishiyama, Ryunosuke Fujita, Shunichi Kubota, Miwa Sasagawa, Tatsuya Nishi
The optically active 3-cyclohexene-1-carboxylic acid was synthesized through a TiCl4-catalyzed diastereoselective Diels–Alder reaction utilizing lactic acid ester as a chiral auxiliary, which can be removed by washing with H2O. The (S)- and (R)-isomers were both derived from easily available ethyl l-lactate. The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.oprd.1c00430. General remarks, general procedure for acryloylation of ethyl acetate, mesylation of ethyl l-lactate, synthesis of D7a utilizing L10a through stereoinversion, general procedure for the diastereoselective Diels–Alder reaction, synthesis of ester derivatives for the Diels–Alder reaction, Diels–Alder reaction with L7a, synthesis of substrate for hydrolysis, general procedure for hydrolysis under basic conditions followed by liquid separation using L8a, sample preparation for (R)-1 and (S)-1, diversification, and 1H and 13C NMR spectra of the compounds (PDF) This article has not yet been cited by other publications.

Publisher URL: https://pubs.acs.org/doi/10.1021/acs.oprd.1c00430

DOI: 10.1021/acs.oprd.1c00430

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