Sharpless asymmetric amino-hydroxylation

  • Chapter
  • First Online:
Name Reactions
  • 309 Accesses

Abstract

Osmium-mediated cis-addition of nitrogen and oxygen to olefins. Regioselectivity may be controlled by ligand. Nitrogen sources (X–NClNa) include

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Chapter
EUR 29.95
Price includes VAT (Germany)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
EUR 71.68
Price includes VAT (Germany)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
EUR 90.94
Price includes VAT (Germany)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free ship** worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Similar content being viewed by others

References

  1. (a) Herranz, E.; Sharpless, K. B. J. Org. Chem. 1978, 43, 2544–2548. K. Barry Sharpless (USA, 1941–) shared the Nobel Prize in Chemistry in 2001 with Herbert William S. Knowles (USA, 1917–) and Ryoji Noyori (Japan, 1938–) for his work on chirally catalyzed oxidation reactions. (b) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem. Int. Ed. 1996, 35, 2813–2817. (c) Rubin, A. E.; Sharpless, K. B. Angew. Chem. Int. Ed. 1997, 36, 2637–2640. (d) Kolb, H. C.; Sharpless, K. B. Transition Met. Org. Synth. 1998, 2, 243–260. (Review). (e) Thomas, A.; Sharpless, K. B. J. Org. Chem. 1999, 64, 8379–8385. (f) Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783–786.

    Google Scholar 

  2. Nicolaou, K. C.; Boddy, C. N. C.; Li, H.; Koumbis, A. E.; Hughes, R.; Natarajan, S.; Jain, N. F.; Ramanjulu, J. M.; Braese, S.; Solomon, M. E. Chem. Eur. J. 1999, 5, 2602–2621.

    Google Scholar 

  3. Lohr, B.; Orlich, S.; Kunz, H. Synlett 1999, 1139–1141.

    Google Scholar 

  4. Boger, D. L.; Lee, R. J.; Bounaud, P.-Y.; Meier, P. J. Org. Chem. 2000, 65, 6770–6772.

    Article  CAS  Google Scholar 

  5. Demko, Z. P.; Bartsch, M.; Sharpless, K. B. Org. Lett. 2000, 2, 2221–2223.

    Article  CAS  Google Scholar 

  6. Barta, N. S.; Sidler, D. R.; Somerville, K. B.; Weissman, S. A.; Larsen, R. D.; Reider, P. J. Org. Lett. 2000, 2, 2821–2824.

    Article  CAS  Google Scholar 

  7. Bolm, C.; Hildebrand, J. P.; Muñiz, K. In Catalytic Asymmetric Synthesis; 2nd edn., Ojima, I., Ed.; Wiley–VCH: New York, 2000, 399. (Review).

    Google Scholar 

  8. Bodkin, J. A.; McLeod, M. D. J. Chem. Soc., Perkin 1 2002, 2733–2746. (Review).

    Google Scholar 

  9. Rahman, N. A.; Landais, Y. Cur. Org. Chem. 2000, 6, 1369–1395. (Review).

    Google Scholar 

  10. Nilov, D.; Reiser, O. Recent Advances on the Sharpless Asymmetric Aminohydroxylation. In Organic Synthesis Highlights Schmalz, H.-G.; Wirth, T., eds.; Wiley–VCH: Weinheim, Germany 2003, 118–124. (Review).

    Google Scholar 

  11. Bodkin, J. A.; Bacskay, G. B.; McLeod, M. D. Org. Biomol. Chem. 2008, 6, 2544–2553.

    Article  CAS  Google Scholar 

  12. Wong, D.; Taylor, C. M. Tetrahedron Lett. 2009, 50, 1273–1275.

    Article  CAS  Google Scholar 

  13. Harris, L.; Mee, S. P. H.; Furneaux, R. H.; Gainsford, G. J.; Luxenburger, A. J. Org. Chem. 2011, 76, 358–372.

    Article  CAS  Google Scholar 

  14. Kumar, J. N.; Das, B. Tetrahedron Lett. 2013, 54, 3865–3867.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Li, J.J. (2014). Sharpless asymmetric amino-hydroxylation. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_248

Download citation

Publish with us

Policies and ethics

Navigation