Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis |
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Authors: | Ann M Chippindale Stephen G Davies Keiji IwamotoRichard M Parkin Christian AP SmethurstAndrew D Smith Humberto Rodriguez-Solla |
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Institution: | a Chemical Crystallography Laboratory, University of Oxford, 9 Parks Road, Oxford OX1 3PD, UK b The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QY, UK |
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Abstract: | Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters followed by ring closing metathesis is used to afford efficiently a range of substituted cyclic β-amino esters in high d.e. Alternatively, conjugate addition to α,β-unsaturated Weinreb amides, functional group conversion and ring closing metathesis affords cyclic amines in high d.e. The further application of this methodology to the synthesis of a range of carbocyclic β-amino esters via conjugate addition, enolate alkylation and ring closing metathesis is also described. Application of this methodology affords, after deprotection, (S)-homoproline, (S)-homopipecolic acid, (S)-coniine and (1S,2S)-trans-pentacin. |
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Keywords: | lithium amide conjugate addition ring closing metathesis |
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