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Organocatalytic enantioselective cascade Michael-Michael-Wittig reactions of phosphorus ylides: one-pot synthesis of the all-cis trisubstituted cyclohexenecarboxylates via the [1 + 2 + 3] annulation.
Org Lett. 2009 Nov 19; 11(22):5246-9.OL

Abstract

The stereoselective synthesis of all-cis 5-nitro-4,6-diphenylcyclohex-1-enecarboxylic ester has been achieved by an organocatalytic asymmetric Michael-Michael-Wittig cascade reaction of phosphorus ylides, nitroolefins, and alpha,beta-unsaturated aldehydes with excellent enantioselectivities (up to >99% ee).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Hong BC
Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621, Taiwan, ROC. chebch@ccu.edu.tw
Jan RH
No affiliation info available
Tsai CW
No affiliation info available
Nimje RY
No affiliation info available
Liao JH
No affiliation info available
Lee GH
No affiliation info available

MeSH

AldehydesAlkenesCatalysisCrystallography, X-RayCyclohexenesModels, MolecularMolecular StructureNitro CompoundsOrganophosphorus CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19852490

Citation

Hong, Bor-Cherng, et al. "Organocatalytic Enantioselective Cascade Michael-Michael-Wittig Reactions of Phosphorus Ylides: One-pot Synthesis of the All-cis Trisubstituted Cyclohexenecarboxylates Via the [1 + 2 + 3] Annulation." Organic Letters, vol. 11, no. 22, 2009, pp. 5246-9.
Hong BC, Jan RH, Tsai CW, et al. Organocatalytic enantioselective cascade Michael-Michael-Wittig reactions of phosphorus ylides: one-pot synthesis of the all-cis trisubstituted cyclohexenecarboxylates via the [1 + 2 + 3] annulation. Org Lett. 2009;11(22):5246-9.
Hong, B. C., Jan, R. H., Tsai, C. W., Nimje, R. Y., Liao, J. H., & Lee, G. H. (2009). Organocatalytic enantioselective cascade Michael-Michael-Wittig reactions of phosphorus ylides: one-pot synthesis of the all-cis trisubstituted cyclohexenecarboxylates via the [1 + 2 + 3] annulation. Organic Letters, 11(22), 5246-9. https://doi.org/10.1021/ol9021832
Hong BC, et al. Organocatalytic Enantioselective Cascade Michael-Michael-Wittig Reactions of Phosphorus Ylides: One-pot Synthesis of the All-cis Trisubstituted Cyclohexenecarboxylates Via the [1 + 2 + 3] Annulation. Org Lett. 2009 Nov 19;11(22):5246-9. PubMed PMID: 19852490.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic enantioselective cascade Michael-Michael-Wittig reactions of phosphorus ylides: one-pot synthesis of the all-cis trisubstituted cyclohexenecarboxylates via the [1 + 2 + 3] annulation. AU - Hong,Bor-Cherng, AU - Jan,Rei-Hau, AU - Tsai,Chih-Wei, AU - Nimje,Roshan Y, AU - Liao,Ju-Hsiou, AU - Lee,Gene-Hsiang, PY - 2009/10/27/entrez PY - 2009/10/27/pubmed PY - 2010/1/15/medline SP - 5246 EP - 9 JF - Organic letters JO - Org Lett VL - 11 IS - 22 N2 - The stereoselective synthesis of all-cis 5-nitro-4,6-diphenylcyclohex-1-enecarboxylic ester has been achieved by an organocatalytic asymmetric Michael-Michael-Wittig cascade reaction of phosphorus ylides, nitroolefins, and alpha,beta-unsaturated aldehydes with excellent enantioselectivities (up to >99% ee). SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19852490/Organocatalytic_enantioselective_cascade_Michael_Michael_Wittig_reactions_of_phosphorus_ylides:_one_pot_synthesis_of_the_all_cis_trisubstituted_cyclohexenecarboxylates_via_the_[1_+_2_+_3]_annulation_ L2 - https://doi.org/10.1021/ol9021832 DB - PRIME DP - Unbound Medicine ER -