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Dihydroxylation-based approach for the asymmetric syntheses of hydroxy-gamma-butyrolactones


Reference:

Peed, J., Davies, I. R., Peacock, L. R., Taylor, J. E., Kociok-Kohn, G. and Bull, S. D., 2012. Dihydroxylation-based approach for the asymmetric syntheses of hydroxy-gamma-butyrolactones. Journal of Organic Chemistry, 77 (1), pp. 543-555.

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    Official URL:

    http://dx.doi.org/10.1021/jo2021289

    Abstract

    A method of preparing enantiopure hydroxy-gamma-butyrolactones containing multiple contiguous stereocenters in high yield with good diastereoselectivity has been developed. Osmium tetroxide mediated dihydroxylation of a range of beta-alkenyl-beta-hydroxy-N-acyloxazolidin-2-ones results in formation of triols that undergo spontaneous intramolecular 5-exo-trig cyclization reactions to provide hydroxy-gamma-butyrolactones. The stereochemistry of these hydroxy-gamma-butyrolactones has been established using NOE spectroscopy, which revealed that 1-substituted, 1,1-disubstituted, (E)-1,2-disubstituted, (Z)-1,2-disubstituted, and 1,1,2-trisubstituted alkenes undergo dihydroxylation with anti-diastereoselectivity, while 1,2,2-trisubstituted systems afford syn-diastereoisomers. The synthetic utility of this methodology has been demonstrated for the asymmetric synthesis of the natural product 2-deoxy-D-ribonolactone.

    Details

    Item Type Articles
    CreatorsPeed, J., Davies, I. R., Peacock, L. R., Taylor, J. E., Kociok-Kohn, G. and Bull, S. D.
    DOI10.1021/jo2021289
    DepartmentsFaculty of Science > Chemistry
    Publisher StatementTaylor_JOC_2012_77_1_543.pdf: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo2021289; Taylor_JOC_2012_77_1_543.doc: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo2021289
    RefereedYes
    StatusPublished
    ID Code28747

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