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A highly efficient asymmetric synthesis of vernakalant.
Org Lett
May 2014
Department of Process Chemistry, Merck Research Laboratories, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
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.
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Angew Chem Int Ed Engl
May 2013
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China.
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