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Synfacts 2010(3): 0258-0258
DOI: 10.1055/s-0029-1219298
DOI: 10.1055/s-0029-1219298
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Formal Synthesis of (+)-Indatraline
K. Yoo, H. Kim, J. Yun*
Sungkyunkwan University, Suwon, South Korea
Further Information
Publication History
Publication Date:
18 February 2010 (online)
Significance
The key step in this formal synthesis of (+)-indatraline is a catalytic asymmetric conjugate reduction (B → C) of a β,β-diaryl-α,β-unsaturated nitrile using a copper hydride coordinated to (R)-Josiphos. A further eleven examples are reported (78-91% yield) with typical ee values exceeding 90% even in cases where the two aryl groups have a similar steric demand.