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Organocatalytic asymmetric robinson annulation of alpha,beta-unsaturated aldehydes: applications to the total synthesis of (+)-palitantin.
J Org Chem. 2007 Oct 26; 72(22):8459-71.JO

Abstract

The highly enantioselective organocatalytic Robinson annulation of alpha,beta-unsaturated aldehydes was achieved, catalyzed by l-proline and trialkylamines and providing the formal [4 + 2] cycloaddition adducts. Additionally, in some examples in the catalysis with diarylpyrrolinol silyl ethers, the reactions afforded the [4 + 2] adducts with high enantioselectivity (>99.5% ee). The structure of the adduct, obtained from the reaction of 3-methylbut-2-enal and (E)-3-(2-nitrophenyl)acrylaldehyde, was confirmed by X-ray analysis. The absolute configurations of some [4 + 2] cycloadducts were investigated, and the methodology was applied in the synthesis of (+)-palitantin.

Authors+Show Affiliations

Hong BC
Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621 Taiwan, ROC. chebch@ccu.edu.tw
Wu MF
No affiliation info available
Tseng HC
No affiliation info available
Huang GF
No affiliation info available
Su CF
No affiliation info available
Liao JH
No affiliation info available

MeSH

AldehydesAminesCatalysisCrystallography, X-RayCyclizationCyclohexanolsCyclohexanonesModels, MolecularMolecular StructureProlineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

17919000

Citation

Hong, Bor-Cherng, et al. "Organocatalytic Asymmetric Robinson Annulation of Alpha,beta-unsaturated Aldehydes: Applications to the Total Synthesis of (+)-palitantin." The Journal of Organic Chemistry, vol. 72, no. 22, 2007, pp. 8459-71.
Hong BC, Wu MF, Tseng HC, et al. Organocatalytic asymmetric robinson annulation of alpha,beta-unsaturated aldehydes: applications to the total synthesis of (+)-palitantin. J Org Chem. 2007;72(22):8459-71.
Hong, B. C., Wu, M. F., Tseng, H. C., Huang, G. F., Su, C. F., & Liao, J. H. (2007). Organocatalytic asymmetric robinson annulation of alpha,beta-unsaturated aldehydes: applications to the total synthesis of (+)-palitantin. The Journal of Organic Chemistry, 72(22), 8459-71.
Hong BC, et al. Organocatalytic Asymmetric Robinson Annulation of Alpha,beta-unsaturated Aldehydes: Applications to the Total Synthesis of (+)-palitantin. J Org Chem. 2007 Oct 26;72(22):8459-71. PubMed PMID: 17919000.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic asymmetric robinson annulation of alpha,beta-unsaturated aldehydes: applications to the total synthesis of (+)-palitantin. AU - Hong,Bor-Cherng, AU - Wu,Ming-Fun, AU - Tseng,Hsing-Chang, AU - Huang,Guo-Fong, AU - Su,Cheng-Feng, AU - Liao,Ju-Hsiou, Y1 - 2007/10/06/ PY - 2007/10/9/pubmed PY - 2008/1/8/medline PY - 2007/10/9/entrez SP - 8459 EP - 71 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 22 N2 - The highly enantioselective organocatalytic Robinson annulation of alpha,beta-unsaturated aldehydes was achieved, catalyzed by l-proline and trialkylamines and providing the formal [4 + 2] cycloaddition adducts. Additionally, in some examples in the catalysis with diarylpyrrolinol silyl ethers, the reactions afforded the [4 + 2] adducts with high enantioselectivity (>99.5% ee). The structure of the adduct, obtained from the reaction of 3-methylbut-2-enal and (E)-3-(2-nitrophenyl)acrylaldehyde, was confirmed by X-ray analysis. The absolute configurations of some [4 + 2] cycloadducts were investigated, and the methodology was applied in the synthesis of (+)-palitantin. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17919000/Organocatalytic_asymmetric_robinson_annulation_of_alphabeta_unsaturated_aldehydes:_applications_to_the_total_synthesis_of__+__palitantin_ L2 - https://doi.org/10.1021/jo701477v DB - PRIME DP - Unbound Medicine ER -