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Phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita-Baylis-Hillman carbonates with C,N-cyclic azomethine imines.
J Am Chem Soc. 2015 Apr 08; 137(13):4316-9.JA

Abstract

The first phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita-Baylis-Hillman carbonates with C,N-cyclic azomethine imines is described. Using a spirocyclic chiral phosphine as the catalyst, a novel class of pharmaceutically interesting 4,6,7,11b-tetrahydro-1H-pyridazino[6,1-a]iso-quinoline derivatives were obtained in high yields with good to excellent diastereoselectivities and extremely excellent enantioselectivities (98->99% ee).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhang L
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China.
Liu H
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China.
Qiao G
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China.
Hou Z
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China.
Liu Y
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China.
Xiao Y
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China.
Guo H
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China.

MeSH

Azo CompoundsCarbonatesCatalysisCycloaddition ReactionIminesPhosphinesStereoisomerismThiosemicarbazones

Pub Type(s)

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

Language

eng

PubMed ID

25799312

Citation

Zhang, Lei, et al. "Phosphine-catalyzed Highly Enantioselective [3 + 3] Cycloaddition of Morita-Baylis-Hillman Carbonates With C,N-cyclic Azomethine Imines." Journal of the American Chemical Society, vol. 137, no. 13, 2015, pp. 4316-9.
Zhang L, Liu H, Qiao G, et al. Phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita-Baylis-Hillman carbonates with C,N-cyclic azomethine imines. J Am Chem Soc. 2015;137(13):4316-9.
Zhang, L., Liu, H., Qiao, G., Hou, Z., Liu, Y., Xiao, Y., & Guo, H. (2015). Phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita-Baylis-Hillman carbonates with C,N-cyclic azomethine imines. Journal of the American Chemical Society, 137(13), 4316-9. https://doi.org/10.1021/jacs.5b01138
Zhang L, et al. Phosphine-catalyzed Highly Enantioselective [3 + 3] Cycloaddition of Morita-Baylis-Hillman Carbonates With C,N-cyclic Azomethine Imines. J Am Chem Soc. 2015 Apr 8;137(13):4316-9. PubMed PMID: 25799312.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita-Baylis-Hillman carbonates with C,N-cyclic azomethine imines. AU - Zhang,Lei, AU - Liu,Honglei, AU - Qiao,Guanyu, AU - Hou,Zhanfeng, AU - Liu,Yang, AU - Xiao,Yumei, AU - Guo,Hongchao, Y1 - 2015/03/27/ PY - 2015/3/24/entrez PY - 2015/3/24/pubmed PY - 2016/3/18/medline SP - 4316 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 137 IS - 13 N2 - The first phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita-Baylis-Hillman carbonates with C,N-cyclic azomethine imines is described. Using a spirocyclic chiral phosphine as the catalyst, a novel class of pharmaceutically interesting 4,6,7,11b-tetrahydro-1H-pyridazino[6,1-a]iso-quinoline derivatives were obtained in high yields with good to excellent diastereoselectivities and extremely excellent enantioselectivities (98->99% ee). SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/25799312/Phosphine_catalyzed_highly_enantioselective_[3_+_3]_cycloaddition_of_Morita_Baylis_Hillman_carbonates_with_CN_cyclic_azomethine_imines_ DB - PRIME DP - Unbound Medicine ER -