A Highly Efficient Asymmetric Synthesis of Vernakalant
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- 作者：John Limanto ; Eric R. Ashley ; Jingjun Yin ; Gregory L. Beutner ; Brendan T. Grau ; Amude M. Kassim ; Mary M. Kim ; Artis Klapars ; Zhijian Liu ; Hallena R. Strotman ; Matthew D. Truppo
- 刊名：Organic Letters
- 出版年：2014
- 出版时间：May 16, 2014
- 年：2014
- 卷：16
- 期：10
- 页码：2716-2719
- 全文大小：246K
- 年卷期：v.16,no.10(May 16, 2014)
- ISSN：1523-7052
文摘
A novel synthesis of vernakalant is described. Using inexpensive and readily available reagents, the key transformations involve (1) an efficient zinc-amine-promoted etherification, (2) a highly stereoselective enzyme-catalyzed dynamic asymmetric transamination to set up the two contiguous chiral centers in the cyclohexane ring, and (3) a pyrrolidine ring formation via alkyl-B(OH)2-catalyzed amidation and subsequent imide reduction.