Efficient asymmetric synthesis of quaternary (E)-vinylglycines by deconjugative alkylation of dehydroamino acids |
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Authors: | Jones Matthew C Marsden Stephen P Muñoz Subtil Dulce M |
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Institution: | School of Chemistry, University of Leeds, Leeds LS2 9JT, UK. |
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Abstract: | A two-step protocol for the asymmetric synthesis of protected quaternary (E)-vinylglycines from simple aldehydes is reported. The key step is a regiocontrolled deconjugative asymmetric alkylation of dehydroamino acids, giving the targets as single geometric isomers with high diastereoselectivity (92-96% de). The products can be converted to valuable quaternary beta-amino alcohols by chemoselective reduction. reaction: see text]. |
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