Self-condensation of N-tert-butanesulfinyl aldimines: application to the rapid asymmetric synthesis of biologically important amine-containing compounds.
[reaction: see text] Highly diastereoselective intra- and intermolecular self-condensation reactions of N-tert-butanesulfinyl aldimines have been developed and applied to the rapid, asymmetric synthesis of trans-2-aminocyclopentanecarboxylic acid and the drug candidate SC-53116. Key to both syntheses is a novel microwave-assisted reaction in which N-sulfinyl aldimines are cleanly converted into nitriles in high-yielding concerted elimination processes.
Schenkel
Laurie B
LB
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.
Ellman
Jonathan A
JA
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001549:Benzamides / Q000138:chemical synthesis*; D002384:Catalysis; D007202:Indicators and Reagents; D008872:Microwaves; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*
D000588:Amines; D001549:Benzamides; D007202:Indicators and Reagents; D009570:Nitriles; D011758:Pyrroles; C074211:SC 53116