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. 2013 Mar 11;52(11):3195-8.
doi: 10.1002/anie.201209863. Epub 2013 Jan 31.

Protecting-group-free diastereoselective C-C coupling of 1,3-glycols and allyl acetate through site-selective primary alcohol dehydrogenation

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Protecting-group-free diastereoselective C-C coupling of 1,3-glycols and allyl acetate through site-selective primary alcohol dehydrogenation

Anne-Marie R Dechert-Schmitt et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Figure 1
Figure 1
Cyclometallated iridium catalysts for site-selective allylation.
Scheme 1
Scheme 1
Site selective dehydrogenation enables protecting group-free allylation of diols.
Scheme 2
Scheme 2
Synthesis of the C11-C18 fragment of RK-397.a aAs described for Table 1.

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References

    1. The term chemoselectivity broadly refers to the ability to selectively act upon like or unlike functional groups: Trost BM. Science. 1983;219:245–250. The term site-selectivity will be used in the more specific context of discrimination between like functional groups en route to constitutionally isomeric products.

    1. Young IS, Baran PS. Nature Chem. 2009;1:193–205. - PubMed
    1. Griswold KS, Miller SJ. Tetrahedron. 2003;59:8869–8875.
    2. Lewis CA, Sculimbrene BR, Xu Y, Miller SJ. Org Lett. 2005;7:3021–3023. - PubMed
    3. Lewis CA, Miller SJ. Angew Chem. 2006;118:5744–5747.
    4. Angew Chem Int Ed. 2006;45:5616–5619. - PubMed
    5. Lewis CA, Merkel J, Miller SJ. Bioorg Med Chem Lett. 2008;18:6007–6011. - PMC - PubMed
    6. Lewis CA, Longcore KE, Miller SJ, Wender PA. J Nat Prod. 2009;72:1864–1869. - PMC - PubMed
    7. Fowler BS, Laemmerhold KM, Miller SJ. J Am Chem Soc. 2012;134:9755–9761. - PMC - PubMed
    1. Lee D, Taylor MS. J Am Chem Soc. 2011;133:3724–3727. - PubMed
    2. Chan L, Taylor MS. Org Lett. 2011;13:3090–3093. - PubMed
    3. Gouliaras C, Lee D, Chan L, Taylor MS. J Am Chem Soc. 2011;133:13926–13929. - PubMed
    4. Lee D, Williamson CL, Chan L, Taylor MS. J Am Chem Soc. 2012;134:8260–8267. - PubMed
    1. For reviews on site-selective metal catalyzed cross-coupling of polyhalogenated molecules, see: Fairlamb IJS. Chem Soc Rev. 2007;36:1036–1045.Joucla L, Djakovitch L. Adv Synth Catal. 2009;351:673–714.Wang JR, Manabe K. Synthesis. 2009:1405–1427.Rossi R, Bellina F, Lessi M. Adv Synth Catal. 2012;354:1181–1255.

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