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. 2013 May 1;135(17):6419-22.
doi: 10.1021/ja401867b. Epub 2013 Apr 19.

Catalytic, enantioselective, intramolecular carbosulfenylation of olefins

Affiliations

Catalytic, enantioselective, intramolecular carbosulfenylation of olefins

Scott E Denmark et al. J Am Chem Soc. .

Abstract

The first catalytic, enantioselective carbosulfenylation of alkenes with an aromatic nucleophile is described, using a BINAM-based selenophosphoramide catalyst. E-Alkyl- and aryl-substituted alkenes afforded tetrahydronaphthalenes with complete diastereospecificity, and generally high enantiomeric ratios.

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Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2

References

    1. de la Mare PBD, Bolton R. In: Electrophilic Additions to Unsaturated Systems. 2nd Ed. de la Mare PBD, Bolton R, editors. Vol. 9. Amsterdam: Elsevier; 1982. pp. 198–246.
    1. Schmid GH. Supplement A: The chemistry of double bonded functional groups. 1989;Vol. Volume 2(Part 1):679–731.
    2. Schmid GH, Garratt DG. The chemistry of double-bonded functional groups Part 2. London: John Wiley & Sons; 1977. pp. 725–912.
    3. Lucchini V, Modena G, Pasquato L. Gazz. Chim. Ital. 1997;127(4):177–188.
    4. Rayner CM. In: Organosulfur Chemistry: Synthetic Aspects. Page P, editor. London: Academic Press; 1995. pp. 89–131.
    5. Modena G, Pasquato L, Lucchini V. Phosphorus, Sulfur Silicon Relat. Elem. 1994;95-6(1–4):265–282.
    6. Capozzi G, Modena G, Pasquato L. In: The Chemistry of Sulphenic Acids and Their Derivatives. Patai S, editor. West Sussex: John Wiley & Sons Ltd; 1990. pp. 403–516.
    7. Harring SR, Edstrom ED, Livinghouse T. Adv. Heterocyclic Nat. Prod. Synth. 1992;2:299–376.
    8. Capozzi G, Modena G. In: Organic Sulfur Chemistry: Theoretical and Experimental Advances. Bernardi F, Csizmadia IG, Mangini A, editors. Vol. 19. Amsterdam: Elsevier; 1985. pp. 246–298.
    1. Drabowicz J, Lyzwa P, Mikolajczyk M. In: The Chemistry of Sulphenic Acids and Their Derivatives. Patai S, editor. West Sussex: John Wiley & Sons Ltd; 1990. pp. 187–220.
    2. Drabowicz J, Kielbasinski P, Mikolajczyk M. In: The Chemistry of Sulphenic Acids and Their Derivatives. Patai S, editor. West Sussex: John Wiley & Sons Ltd; 1990. pp. 221–292.
    1. Hogg DR. In: The Chemistry of Sulphenic Acids and Their Derivatives. Patai S, editor. West Sussex: John Wiley & Sons Ltd; 1990. pp. 361–402.
    1. Moore JT, Soldi C, Fettinger JC, Shaw JT. Chem. Sci. 2013:292–296. - PMC - PubMed
    2. Edstrom ED, Livinghouse T. J. Org. Chem. 1987;52:949–951.
    3. Masaki Y, Hashimoto K, Sakuma K, Kaji K. Tetrahedron Lett. 1982:1481–1484.

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