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

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• 作者：Ephraim M. Bassan ; Carl A. Baxter ; Gregory L. Beutner ; Khateeta M. Emerson ; Fred J. Fleitz ; Simon Johnson ; Stephen Keen ; Mary M. Kim ; Jeffrey T. Kuethe ; William R. Leonard ; Peter R. Mullens ; Daniel J. Muzzio ; Christopher Roberge ; Nobuyoshi Yasuda
• 刊名：Organic Process Research & Development
• 出版年：2012
• 出版时间：January 20, 2012
• 年：2012
• 卷：16
• 期：1
• 页码：87-95
• 全文大小：982K
• 年卷期：v.16,no.1(January 20, 2012)
• ISSN：1520-586X

文摘

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 multikilogram scale.