Multikilogram-Scale Synthesis of a Chiral Cyclopropanol and an Investigation of the Safe Use of Lithium Acetylide–Ethylene Diamine Complex

…, S Johnson, S Keen, MM Kim, JT Kuethe…

Index: Bassan, Ephraim M.; Baxter, Carl A.; Beutner, Gregory L.; Emerson, Khateeta M.; Fleitz, Fred J.; Johnson, Simon; Keen, Stephen; Kim, Mary M.; Kuethe, Jeffrey T.; Leonard, William R.; Mullens, Peter R.; Muzzio, Daniel J.; Roberge, Christopher; Yasuda, Nobuyoshi Organic Process Research and Development, 2012 , vol. 16, # 1 p. 87 - 95

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Citation Number: 9

Abstract

A six-step route starting from a readily available vinyl boronate was identified to produce an enantioenriched cyclopropanol in an overall 16% yield. Key steps involve the use of lithium acetylide-ethylene diamine complex 5 and an enzymatic resolution of a racemic cyclopropanol acetate. Process safety considerations surrounding the use of 5 were examined, and an improved procedure is described which was safely demonstrated at ...