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Dual organocatalysis: asymmetric allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates.
Chemistry. 2009; 15(7):1574-7.C

Abstract

The first highly enantioselective allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates by dual catalysis of (DHQD)(2)AQN and (S)-BINOL has been investigated. Excellent stereoselectivities have been achieved for a broad spectrum of substrates (d.r. > 99:1, up to 99 % ee). The multifunctional allylic products could be efficiently converted to a range of complex chiral cyclic frameworks. EWG = electron-withdrawing group, (DHQD)(2)AQN = hydroquinidine (anthraquinone-1,4-diyl) diether, (S)-BINOL = (S)-(-)-1,1'-bi-2-naphthol.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Cui HL
Key laboratory of Drug-Targeting and Drug Delivery Systems of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, China.
Peng J
No affiliation info available
Feng X
No affiliation info available
Du W
No affiliation info available
Jiang K
No affiliation info available
Chen YC
No affiliation info available

MeSH

AlkenesAlkylationAnthraquinonesCarbonatesCatalysisCyclohexenesEthersIsomerismNaphthols

Pub Type(s)

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

Language

eng

PubMed ID

19132709

Citation

Cui, Hai-Lei, et al. "Dual Organocatalysis: Asymmetric Allylic-allylic Alkylation of Alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman Carbonates." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 15, no. 7, 2009, pp. 1574-7.
Cui HL, Peng J, Feng X, et al. Dual organocatalysis: asymmetric allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates. Chemistry. 2009;15(7):1574-7.
Cui, H. L., Peng, J., Feng, X., Du, W., Jiang, K., & Chen, Y. C. (2009). Dual organocatalysis: asymmetric allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates. Chemistry (Weinheim an Der Bergstrasse, Germany), 15(7), 1574-7. https://doi.org/10.1002/chem.200802534
Cui HL, et al. Dual Organocatalysis: Asymmetric Allylic-allylic Alkylation of Alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman Carbonates. Chemistry. 2009;15(7):1574-7. PubMed PMID: 19132709.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Dual organocatalysis: asymmetric allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates. AU - Cui,Hai-Lei, AU - Peng,Jing, AU - Feng,Xin, AU - Du,Wei, AU - Jiang,Kun, AU - Chen,Ying-Chun, PY - 2009/1/10/entrez PY - 2009/1/10/pubmed PY - 2009/3/5/medline SP - 1574 EP - 7 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 15 IS - 7 N2 - The first highly enantioselective allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates by dual catalysis of (DHQD)(2)AQN and (S)-BINOL has been investigated. Excellent stereoselectivities have been achieved for a broad spectrum of substrates (d.r. > 99:1, up to 99 % ee). The multifunctional allylic products could be efficiently converted to a range of complex chiral cyclic frameworks. EWG = electron-withdrawing group, (DHQD)(2)AQN = hydroquinidine (anthraquinone-1,4-diyl) diether, (S)-BINOL = (S)-(-)-1,1'-bi-2-naphthol. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/19132709/Dual_organocatalysis:_asymmetric_allylic_allylic_alkylation_of_alphaalpha_dicyanoalkenes_and_Morita_Baylis_Hillman_carbonates_ L2 - https://doi.org/10.1002/chem.200802534 DB - PRIME DP - Unbound Medicine ER -