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Highly stereoselective oxy-Michael additions to alpha,beta-disubstituted nitro olefins: asymmetric synthesis of pseudo-norephedrine derivatives and THP* protected alpha-hydroxy ketones.
Org Biomol Chem. 2004 Oct 21; 2(20):2932-4.OB

Abstract

The "naked" anion of (S)-6-methyl delta lactol undergoes efficient oxy-Michael addition to alpha,beta-disubstituted nitro olefins to give the THP* protected Henry products with excellent (95-->98% de) stereocontrol at the beta-position and moderate (up to 3 : 1) stereocontrol at the alpha-position in favour of the syn-diastereoisomer. Nitro group reduction with in situN-Boc protection and THP* removal provides alpha,beta-disubstituted ethanolamine derivatives, while treatment with tetrapropylammonium perruthenate gives THP* protected alpha-hydroxy ketone derivatives in high diasteromeric excess.

Authors+Show Affiliations

Buchanan DJ
Department of Chemistry, University of Cambridge, UK.
Dixon DJ
No affiliation info available
Hernandez-Juan FA
No affiliation info available

MeSH

AlkenesKetonesModels, ChemicalModels, MolecularMolecular StructurePhenylpropanolamineStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15480457

Citation

Buchanan, David J., et al. "Highly Stereoselective oxy-Michael Additions to Alpha,beta-disubstituted Nitro Olefins: Asymmetric Synthesis of Pseudo-norephedrine Derivatives and THP* Protected Alpha-hydroxy Ketones." Organic & Biomolecular Chemistry, vol. 2, no. 20, 2004, pp. 2932-4.
Buchanan DJ, Dixon DJ, Hernandez-Juan FA. Highly stereoselective oxy-Michael additions to alpha,beta-disubstituted nitro olefins: asymmetric synthesis of pseudo-norephedrine derivatives and THP* protected alpha-hydroxy ketones. Org Biomol Chem. 2004;2(20):2932-4.
Buchanan, D. J., Dixon, D. J., & Hernandez-Juan, F. A. (2004). Highly stereoselective oxy-Michael additions to alpha,beta-disubstituted nitro olefins: asymmetric synthesis of pseudo-norephedrine derivatives and THP* protected alpha-hydroxy ketones. Organic & Biomolecular Chemistry, 2(20), 2932-4.
Buchanan DJ, Dixon DJ, Hernandez-Juan FA. Highly Stereoselective oxy-Michael Additions to Alpha,beta-disubstituted Nitro Olefins: Asymmetric Synthesis of Pseudo-norephedrine Derivatives and THP* Protected Alpha-hydroxy Ketones. Org Biomol Chem. 2004 Oct 21;2(20):2932-4. PubMed PMID: 15480457.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly stereoselective oxy-Michael additions to alpha,beta-disubstituted nitro olefins: asymmetric synthesis of pseudo-norephedrine derivatives and THP* protected alpha-hydroxy ketones. AU - Buchanan,David J, AU - Dixon,Darren J, AU - Hernandez-Juan,Felix A, Y1 - 2004/09/22/ PY - 2004/10/14/pubmed PY - 2006/5/17/medline PY - 2004/10/14/entrez SP - 2932 EP - 4 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 2 IS - 20 N2 - The "naked" anion of (S)-6-methyl delta lactol undergoes efficient oxy-Michael addition to alpha,beta-disubstituted nitro olefins to give the THP* protected Henry products with excellent (95-->98% de) stereocontrol at the beta-position and moderate (up to 3 : 1) stereocontrol at the alpha-position in favour of the syn-diastereoisomer. Nitro group reduction with in situN-Boc protection and THP* removal provides alpha,beta-disubstituted ethanolamine derivatives, while treatment with tetrapropylammonium perruthenate gives THP* protected alpha-hydroxy ketone derivatives in high diasteromeric excess. SN - 1477-0520 UR - https://www.unboundmedicine.com/medline/citation/15480457/Highly_stereoselective_oxy_Michael_additions_to_alphabeta_disubstituted_nitro_olefins:_asymmetric_synthesis_of_pseudo_norephedrine_derivatives_and_THP__protected_alpha_hydroxy_ketones_ DB - PRIME DP - Unbound Medicine ER -