Concise and highly selective asymmetric synthesis of acosamine from sorbic acid |
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Authors: | Sharan K. BagalStephen G. Davies Ai M. FletcherJames A. Lee Paul M. RobertsPhilip M. Scott James E. Thomson |
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Affiliation: | a Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK b Pfizer Global R&D, Sandwich, Kent CT13 9NJ, UK |
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Abstract: | Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl)amide to tert-butyl sorbate and subsequent chemo- and diastereoselective ammonium-directed olefinic oxidation of the resultant conjugate addition product {tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-ene} have been used as the key steps in a concise and highly selective asymmetric synthesis of the 2,3,6-trideoxy-3-aminohexose l-acosamine. This sequence of two chemical operations allows rapid assembly of the molecular architecture and facilitates the de novo asymmetric synthesis of methyl N,O-diacetyl-α-l-acosaminide in only 7 steps from commercially available sorbic acid in 15% overall yield. |
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Keywords: | 2,3,6-Trideoxy-3-aminohexose Conjugate addition Ammonium-directed olefinic oxidation Acosamine |
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