A Highly Efficient Asymmetric Synthesis of Vernakalant

A Highly Efficient Asymmetric Synthesis of Vernakalant

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 ce...

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Veröffentlicht in:Organic letters 2014-05, Vol.16 (10), p.2716-2719
Hauptverfasser: Limanto, John, Ashley, Eric R, Yin, Jingjun, Beutner, Gregory L, Grau, Brendan T, Kassim, Amude M, Kim, Mary M, Klapars, Artis, Liu, Zhijian, Strotman, Hallena R, Truppo, Matthew D
Format: Artikel
Sprache:eng
Schlagworte:
Amination
Amines - chemistry
Anisoles - chemical synthesis
Anisoles - chemistry
Catalysis
Chlorides - chemistry
Cyclohexanes
Molecular Structure
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Stereoisomerism
Zinc Compounds - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol501002a