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Aminocatalytic asymmetric exo-Diels-Alder reaction with methiodide salts of Mannich bases and 2,4-dienals to construct chiral spirocycles.
Org Lett. 2013 Feb 15; 15(4):968-71.OL

Abstract

An asymmetric exo-Diels-Alder reaction of α-methylene carbonyl compounds, generated in situ from stable methiodide salts of Mannich bases, with 2,4-dienals, has been developed through trienamine activation of a chiral secondary amine. A spectrum of spirocyclanes with high molecular complexity was efficiently constructed in moderate to excellent diastereo- and enantioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhang SJ
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Zhang J
No affiliation info available
Zhou QQ
No affiliation info available
Dong L
No affiliation info available
Chen YC
No affiliation info available

MeSH

AldehydesBicucullineCatalysisCycloaddition ReactionMannich BasesMolecular StructureSaltsSpiro Compounds

Pub Type(s)

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

Language

eng

PubMed ID

23391251

Citation

Zhang, Shan-Jun, et al. "Aminocatalytic Asymmetric exo-Diels-Alder Reaction With Methiodide Salts of Mannich Bases and 2,4-dienals to Construct Chiral Spirocycles." Organic Letters, vol. 15, no. 4, 2013, pp. 968-71.
Zhang SJ, Zhang J, Zhou QQ, et al. Aminocatalytic asymmetric exo-Diels-Alder reaction with methiodide salts of Mannich bases and 2,4-dienals to construct chiral spirocycles. Org Lett. 2013;15(4):968-71.
Zhang, S. J., Zhang, J., Zhou, Q. Q., Dong, L., & Chen, Y. C. (2013). Aminocatalytic asymmetric exo-Diels-Alder reaction with methiodide salts of Mannich bases and 2,4-dienals to construct chiral spirocycles. Organic Letters, 15(4), 968-71. https://doi.org/10.1021/ol4002015
Zhang SJ, et al. Aminocatalytic Asymmetric exo-Diels-Alder Reaction With Methiodide Salts of Mannich Bases and 2,4-dienals to Construct Chiral Spirocycles. Org Lett. 2013 Feb 15;15(4):968-71. PubMed PMID: 23391251.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Aminocatalytic asymmetric exo-Diels-Alder reaction with methiodide salts of Mannich bases and 2,4-dienals to construct chiral spirocycles. AU - Zhang,Shan-Jun, AU - Zhang,Jun, AU - Zhou,Qing-Qing, AU - Dong,Lin, AU - Chen,Ying-Chun, Y1 - 2013/02/07/ PY - 2013/2/9/entrez PY - 2013/2/9/pubmed PY - 2013/6/26/medline SP - 968 EP - 71 JF - Organic letters JO - Org Lett VL - 15 IS - 4 N2 - An asymmetric exo-Diels-Alder reaction of α-methylene carbonyl compounds, generated in situ from stable methiodide salts of Mannich bases, with 2,4-dienals, has been developed through trienamine activation of a chiral secondary amine. A spectrum of spirocyclanes with high molecular complexity was efficiently constructed in moderate to excellent diastereo- and enantioselectivity. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23391251/Aminocatalytic_asymmetric_exo_Diels_Alder_reaction_with_methiodide_salts_of_Mannich_bases_and_24_dienals_to_construct_chiral_spirocycles_ DB - PRIME DP - Unbound Medicine ER -