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3,3'-bimorpholine derivatives as a new class of organocatalysts for asymmetric Michael addition.
Org Lett. 2006 Jun 08; 8(12):2559-62.OL

Abstract

New N-alkyl-3,3'-bimorpholine derivatives (iPBM) were revealed to be efficient organocatalysts for the asymmetric direct Michael addition of aldehydes to nitroolefins and a vinyl sulfone. In these transformations using iPBM, 1,4-adducts were afforded in high yields, with good to high levels of diastereo- and enantioselectivity. The stereochemical outcome of the reaction could be explained by an acyclic synclinal model. [reaction: see text]

Authors+Show Affiliations

Mossé S
Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland.
Laars M
No affiliation info available
Kriis K
No affiliation info available
Kanger T
No affiliation info available
Alexakis A
No affiliation info available

MeSH

AldehydesAlkenesCatalysisModels, MolecularMolecular StructureMorpholinesNitro CompoundsStereoisomerismVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

16737313

Citation

Mossé, Sarah, et al. "3,3'-bimorpholine Derivatives as a New Class of Organocatalysts for Asymmetric Michael Addition." Organic Letters, vol. 8, no. 12, 2006, pp. 2559-62.
Mossé S, Laars M, Kriis K, et al. 3,3'-bimorpholine derivatives as a new class of organocatalysts for asymmetric Michael addition. Org Lett. 2006;8(12):2559-62.
Mossé, S., Laars, M., Kriis, K., Kanger, T., & Alexakis, A. (2006). 3,3'-bimorpholine derivatives as a new class of organocatalysts for asymmetric Michael addition. Organic Letters, 8(12), 2559-62.
Mossé S, et al. 3,3'-bimorpholine Derivatives as a New Class of Organocatalysts for Asymmetric Michael Addition. Org Lett. 2006 Jun 8;8(12):2559-62. PubMed PMID: 16737313.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 3,3'-bimorpholine derivatives as a new class of organocatalysts for asymmetric Michael addition. AU - Mossé,Sarah, AU - Laars,Marju, AU - Kriis,Kadri, AU - Kanger,Tõnis, AU - Alexakis,Alexandre, PY - 2006/6/2/pubmed PY - 2007/3/27/medline PY - 2006/6/2/entrez SP - 2559 EP - 62 JF - Organic letters JO - Org Lett VL - 8 IS - 12 N2 - New N-alkyl-3,3'-bimorpholine derivatives (iPBM) were revealed to be efficient organocatalysts for the asymmetric direct Michael addition of aldehydes to nitroolefins and a vinyl sulfone. In these transformations using iPBM, 1,4-adducts were afforded in high yields, with good to high levels of diastereo- and enantioselectivity. The stereochemical outcome of the reaction could be explained by an acyclic synclinal model. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16737313/33'_bimorpholine_derivatives_as_a_new_class_of_organocatalysts_for_asymmetric_Michael_addition_ DB - PRIME DP - Unbound Medicine ER -