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Asymmetric direct vinylogous Michael reaction of activated alkenes to nitroolefins catalyzed by modified cinchona alkaloids.
Org Lett. 2005 Nov 10; 7(23):5293-6.OL

Abstract

[reaction: see text] The first organocatalytic and asymmetric direct vinylogous Michael reaction that employs the electron-deficient vinyl malononitriles as the nucleophilic species has been reported. The novel transformations exhibit exclusive gamma-selectivity and high diastereo- and enantioselectivity in the addition to nitroolefins, which give the multifunctional products with two vicinal chiral centers.

Authors+Show Affiliations

Xue D
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Chen YC
No affiliation info available
Wang QW
No affiliation info available
Cun LF
No affiliation info available
Zhu J
No affiliation info available
Deng JG
No affiliation info available

MeSH

AlkenesCatalysisCinchona AlkaloidsMolecular StructureNitro CompoundsStereoisomerismVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

16268561

Citation

Xue, Dong, et al. "Asymmetric Direct Vinylogous Michael Reaction of Activated Alkenes to Nitroolefins Catalyzed By Modified Cinchona Alkaloids." Organic Letters, vol. 7, no. 23, 2005, pp. 5293-6.
Xue D, Chen YC, Wang QW, et al. Asymmetric direct vinylogous Michael reaction of activated alkenes to nitroolefins catalyzed by modified cinchona alkaloids. Org Lett. 2005;7(23):5293-6.
Xue, D., Chen, Y. C., Wang, Q. W., Cun, L. F., Zhu, J., & Deng, J. G. (2005). Asymmetric direct vinylogous Michael reaction of activated alkenes to nitroolefins catalyzed by modified cinchona alkaloids. Organic Letters, 7(23), 5293-6.
Xue D, et al. Asymmetric Direct Vinylogous Michael Reaction of Activated Alkenes to Nitroolefins Catalyzed By Modified Cinchona Alkaloids. Org Lett. 2005 Nov 10;7(23):5293-6. PubMed PMID: 16268561.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric direct vinylogous Michael reaction of activated alkenes to nitroolefins catalyzed by modified cinchona alkaloids. AU - Xue,Dong, AU - Chen,Ying-Chun, AU - Wang,Qi-Wei, AU - Cun,Ling-Feng, AU - Zhu,Jin, AU - Deng,Jin-Gen, PY - 2005/11/5/pubmed PY - 2006/8/10/medline PY - 2005/11/5/entrez SP - 5293 EP - 6 JF - Organic letters JO - Org Lett VL - 7 IS - 23 N2 - [reaction: see text] The first organocatalytic and asymmetric direct vinylogous Michael reaction that employs the electron-deficient vinyl malononitriles as the nucleophilic species has been reported. The novel transformations exhibit exclusive gamma-selectivity and high diastereo- and enantioselectivity in the addition to nitroolefins, which give the multifunctional products with two vicinal chiral centers. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16268561/Asymmetric_direct_vinylogous_Michael_reaction_of_activated_alkenes_to_nitroolefins_catalyzed_by_modified_cinchona_alkaloids_ DB - PRIME DP - Unbound Medicine ER -