Application of the chiral acyl anion equivalent,trans-1,3-dithiane 1,3-dioxide,to an asymmetric synthesis of (R)-salbutamol |
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Authors: | Aggarwal Varinder K Esquivel-Zamora Blanca N |
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Affiliation: | University of Bristol, School of Chemistry, Cantock's Close, BS8, 1TS Bristol, United Kingdom. v.aggarwal@bristol.ac.uk |
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Abstract: | 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. |
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