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Synfacts 2011(1): 0003-0003
DOI: 10.1055/s-0030-1258976
DOI: 10.1055/s-0030-1258976
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of PRC200-SS
Contributor(s):Philip KocienskiP. Valenta, P. J. Carroll, P. J. Walsh*
University of Pennsylvania, Philadelphia, USA
Stereoselective Synthesis of β-Hydroxy Enamines, Aminocyclopropanes, and 1,3-Amino Alcohols via Asymmetric Catalysis
J. Am. Chem. Soc. 2010, 132: 14179-14190
University of Pennsylvania, Philadelphia, USA
Stereoselective Synthesis of β-Hydroxy Enamines, Aminocyclopropanes, and 1,3-Amino Alcohols via Asymmetric Catalysis
J. Am. Chem. Soc. 2010, 132: 14179-14190
Further Information
Publication History
Publication Date:
21 December 2010 (online)
Key words
PRC200-SS - ynamides - β-hydroxy enamines - asymmetric addition - hydroboration
Significance
PRC200-SS is a serotonin-norepinephrine-dopamine reuptake inhibitor and a lead compound for the treatment of depression. This short and efficient synthesis of PRC200-SS features the asymmetric addition of the β-amino alkenyl zinc reagent D to benzaldehyde in the presence of the chiral chaperone E.
Comment
The β-hydroxy (E)-enamine derivative F underwent a hydroxyl-directed diastereoselective hydrogenation via conformation G to give the syn-1,2-disubstituted-1,3-amino alcohol H in moderate yield.