Application of the chiral acyl anion equivalent, trans-1,3-dithiane 1,3-dioxide, to an asymmetric synthesis of (R)-salbutamol.
An enantioselective synthesis of (R)-salbutamol has been carried out using the chiral, C2 symmetric acyl anion equivalent, (1R,3R)-1,3-dithiane 1,3-dioxide, which undergoes addition to an aromatic aldehyde with very high stereocontrol at 0 degrees C. Pummerer reaction and work-up with lithium ethanethiolate generated the alpha-hydroxy thiolester in high yield and further transformations led to the target compound with high enantiomeric excess.
Aggarwal
Varinder K
VK
University of Bristol, School of Chemistry, Cantock's Close, BS8, 1TS Bristol, United Kingdom. v.aggarwal@bristol.ac.uk
Esquivel-Zamora
Blanca N
BN
D000420:Albuterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D006868:Hydrolysis; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013696:Temperature
D000420:Albuterol