An Efficient Chiral Moderator Prepared from Inexpensive (+)-3-Carene: Synthesis of the HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor DPC 963
Organic Letters2000Vol. 2(20), pp. 3119–3121
Citations Over TimeTop 10% of 2000 papers
Goss S. Kauffman, Gregory D. Harris, Roberta L. Dorow, Benjamin R. P. Stone, Rodney L. Parsons, Jaan A. Pesti, Nicholas A. Magnus, Joseph Fortunak, Pat N. Confalone, William A. Nugent
Abstract
The beta-amino alcohol 4 beta-morpholinocaran-3 alpha-ol is prepared by addition of morpholine to alpha-3,4-epoxycarane utilizing anhydrous magnesium bromide as Lewis acid promoter. The enantiopure amino alcohol is uniquely effective as a chiral moderator for the addition of lithium cyclopropylacetylide to an unprotected N-acylketimine. This reaction provides an efficient route to the second generation NNRTI drug candidate DPC 963.
Related Papers
- → Synthesis of Enantiopure 5-Substituted 2,3-Methanopyrrolidines by Cyclization of Enantiopure α-Branched α-N-Homoallylamino Nitriles(2012)8 cited
- → A Valuable Synthetic Route to the Enantiopure Functionalized N‐Substituted Aziridines(2004)1 cited
- → ChemInform Abstract: Efficacious and Rapid Metal‐ and Solvent‐Free Synthesis of Enantiopure Oxazolines.(2015)
- Synthesis of N-Acetyl Morpholine(2007)
- → Stereoselective Addition of Racemic Allenylzinc onto Enantiopure N-tert-Butanesulfinimines(2005)