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Diastereo- and enantioselective [3 + 2] cycloaddition reaction of Morita-Baylis-Hillman carbonates of isatins with N-phenylmaleimide catalyzed by Me-DuPhos.
J Org Chem. 2012 Apr 20; 77(8):4143-7.JO

Abstract

A Me-DuPhos-catalyzed efficient asymmetric [3 + 2] cycloaddition reaction between Morita-Baylis-Hillman carbonates of isatins and N-phenylmaleimide has been developed. This reaction constructs three chiral centers in one step to afford spirocyclopentaneoxindoles in good yields (up to 84%) with excellent diastereo- and enantioselectivies (up to 99% ee).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang Y
Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Liu L
No affiliation info available
Zhang T
No affiliation info available
Zhong NJ
No affiliation info available
Wang D
No affiliation info available
Chen YJ
No affiliation info available

MeSH

CarbonatesCatalysisCyclizationIsatinMaleimidesMolecular StructurePhosphinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22471756

Citation

Wang, Yan, et al. "Diastereo- and Enantioselective [3 + 2] Cycloaddition Reaction of Morita-Baylis-Hillman Carbonates of Isatins With N-phenylmaleimide Catalyzed By Me-DuPhos." The Journal of Organic Chemistry, vol. 77, no. 8, 2012, pp. 4143-7.
Wang Y, Liu L, Zhang T, et al. Diastereo- and enantioselective [3 + 2] cycloaddition reaction of Morita-Baylis-Hillman carbonates of isatins with N-phenylmaleimide catalyzed by Me-DuPhos. J Org Chem. 2012;77(8):4143-7.
Wang, Y., Liu, L., Zhang, T., Zhong, N. J., Wang, D., & Chen, Y. J. (2012). Diastereo- and enantioselective [3 + 2] cycloaddition reaction of Morita-Baylis-Hillman carbonates of isatins with N-phenylmaleimide catalyzed by Me-DuPhos. The Journal of Organic Chemistry, 77(8), 4143-7. https://doi.org/10.1021/jo3002535
Wang Y, et al. Diastereo- and Enantioselective [3 + 2] Cycloaddition Reaction of Morita-Baylis-Hillman Carbonates of Isatins With N-phenylmaleimide Catalyzed By Me-DuPhos. J Org Chem. 2012 Apr 20;77(8):4143-7. PubMed PMID: 22471756.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Diastereo- and enantioselective [3 + 2] cycloaddition reaction of Morita-Baylis-Hillman carbonates of isatins with N-phenylmaleimide catalyzed by Me-DuPhos. AU - Wang,Yan, AU - Liu,Li, AU - Zhang,Tao, AU - Zhong,Neng-Jun, AU - Wang,Dong, AU - Chen,Yong-Jun, Y1 - 2012/04/10/ PY - 2012/4/5/entrez PY - 2012/4/5/pubmed PY - 2012/8/2/medline SP - 4143 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 8 N2 - A Me-DuPhos-catalyzed efficient asymmetric [3 + 2] cycloaddition reaction between Morita-Baylis-Hillman carbonates of isatins and N-phenylmaleimide has been developed. This reaction constructs three chiral centers in one step to afford spirocyclopentaneoxindoles in good yields (up to 84%) with excellent diastereo- and enantioselectivies (up to 99% ee). SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22471756/Diastereo__and_enantioselective_[3_+_2]_cycloaddition_reaction_of_Morita_Baylis_Hillman_carbonates_of_isatins_with_N_phenylmaleimide_catalyzed_by_Me_DuPhos_ L2 - https://doi.org/10.1021/jo3002535 DB - PRIME DP - Unbound Medicine ER -