Synthesis of enantioenriched propargylic alcohols related to polyketide natural products. A comparison of methodologies.
[reaction: see text] Applications of methodology for the synthesis of propargylic alcohols related to polyketide natural products were examined. Noyori's asymmetric transfer hydrogenation of alpha-chiral alkynones was found to be highly selective and catalyst controlled. Additions of TMS acetylene to alpha-chiral aldehydes, catalyzed by a Ti(O-i-Pr)(4)-BINOL complex, were diastereoselective but substrate dependent.
Marshall
James A
JA
Department of Chemistry, P.O. Box 400319 University of Virginia, Charlottesville, Virginia 22904, USA. jam5x@virginia.edu
Bourbeau
Matthew P
MP
D000114:Acetylene / Q000737:chemistry; D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D006865:Hydrogenation; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010755:Organophosphates / Q000737:chemistry*; D010293:Pargyline / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry
D000438:Alcohols; D000447:Aldehydes; D000480:Alkynes; D018942:Macrolides; D009942:Organometallic Compounds; D010755:Organophosphates; D011753:Pyrones; C088526:cytostatin; D012428:Ruthenium; D010293:Pargyline; D000114:Acetylene