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. 2019 Aug 21:26:104409.
doi: 10.1016/j.dib.2019.104409. eCollection 2019 Oct.

Dataset of asymmetric intramolecular [4+3] cycloaddition reactions catalyzed by NHC-gold(I) complexes

Ruoyu Ma  1 , Jianbo Yang  1 , Steven Kelley  2 , Benjamin W Gung  1
Affiliations

Dataset of asymmetric intramolecular [4+3] cycloaddition reactions catalyzed by NHC-gold(I) complexes

Ruoyu Ma et al. Data Brief. .

Abstract

The shared data is the unpublished portion of the experimental section for the article with the title "NHC-Au(I) catalyzed enantioselective intramolecular [4 + 3] cycloaddition of furan propargyl esters".[1] The preparation of the intermediates for chiral NHC-gold(I) complexes and the furan propargyl ester substrates are included in this article. The 1H NMR and 13C NMR spectra of the gold complexes 17a-19c and the X-ray crystal data of 17a, 18a and cycloaddition product 24 are also provided in this article or in Mendeley Data. Finally, the chiral HPLC spectra used to determine enantiomeric excess and Cartesian coordinates of the optimized structure of 25 and 26 calculated by DFT calculation are also presented in the article.

Keywords: Cycloaddition; DFT calculation; Enantioselective; NHC-gold(I) complexes.

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Figures

Fig. 1
Fig. 1
Structures of gold complexes 17a-19c (TMS = Me3Si-; TES = Et3Si-; TPS = Pr3Si-), furan propargyl esters 23, 28, cycloaddition products 24, 29 and DFT calculation models 25 and 26.
Fig. 2
Fig. 2
Crystal structure of the racemic cycloaddition product 24 with four pairs of enantiomers packing in a unit cell. The ester carbonyl group and the dihydrofuran double bond have a syn-relationship.
Fig. 3
Fig. 3
Chrial HPLC spectrum of racemic mixture of cycloaddition product 24.
Fig. 4
Fig. 4
Chrial HPLC spectrum of cycloaddition product 24 with 75% ee.
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Image 17
See this image and copyright information in PMC

References

    1. Ma R., Yang J., Kelley S., Gung B.W. NHC–Au(I)catalyzed enantioselective intramolecular [4+3] cycloaddition of furan propargyl esters. J. Organomet. Chem. 2019;898
    1. Gung B.W., Holmes M.R., Jones C.A., Ma R., Barnes C.L. Structure–enantioselectivity correlation in NHC–Au(I)catalysis for 1,6-enynecyclizations. Tetrahedron Lett. 2016;57:3912–3915.
    1. Campolo D., Arif T., Borie C., Mouysset D., Vanthuyne N., Naubron J.V., Bertrand M.P., Nechab M. Double transfer of chirality in organocopper-mediated bis(alkylating)cycloisomerization of enediynes. Angew. Chem. Int. Ed. 2014;53:3227–3231. - PubMed
    1. Lohse A.G., Hsung R.P. Thermal intramolecular [4 + 2] cycloadditions of allenamides: a stereoselective tandem propargyl amide isomerization-cycloaddition. Org. Lett. 2009;11:3430–3433. - PMC - PubMed
    1. Li G., Zhang G., Zhang L. Au-catalyzed synthesis of (1Z,3E)-2-pivaloxy-1,3-dienes from propargylic pivalates. J. Am. Chem. Soc. 2008;130:3740–3741. - PubMed

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