242
Views
10
CrossRef citations to date
0
Altmetric
GreenChem4

A straightforward green synthesis of N-(tert-butylsulfinyl)imines

, , , &
Pages 1155-1162 | Received 04 Apr 2015, Accepted 09 Nov 2015, Published online: 11 Dec 2015

References

  • Asada, M., M. Iwahashi, T. Obitsu, A. Kinoshita, Y. Nakai, T. Nagase, M. Tanaka, et al. 2010. “3-(2-Aminocarbonylphenyl)Propanoic Acid Analogs as Potent and Selective EP3 Receptor Antagonists. Part 2: Optimization of the Side Chains to Improve In Vitro and In Vivo Potencies.” Bioorganic & Medicinal Chemistry 18: 1641–1658.
  • Coulomb, J., V. Certal, L. Fensterbank, E. Lacôte, and M. Malacria. 2006. “Formation of Cyclic Sulfinates and Sulfinamides Through Homolytic Substitution at the Sulfur Atom.” Angewandte Chemie International Edition 45: 633–637.
  • Davis, F.A. 2006. “Adventures in Sulfur−Nitrogen Chemistry.” Journal of Organic Chemistry 71: 8993–9003.
  • Doering, W.E., and J.D. Chanley. 1946. “The Autoxidation of Quininone.” Journal of the American Chemical Society 68: 586–588.
  • Doering, W.E., G. Cortes, and L.H. Knox. 1947. “Partial Racemization of Quinine.” Journal of the American Chemical Society 69: 1700–1710.
  • Fan, R., D. Pu, F. Wen, Y. Ye, and X. Wang. 2008. “A Facile Synthesis of N-Sulfonyl and N-Sulfinyl Aldimines under Barbier-Type Conditions.” Journal of Organic Chemistry 73: 3623–3625.
  • Ferreira, F., C. Botuha, F. Chemla, and A. Perez-Luna. 2009. “Tert-Butanesulfinimines: Structure, Synthesis and Synthetic Applications.” Chemical Society Reviews 38: 1162–1186.
  • Hua, D.H., N. Lagneau, H. Wang, and J. Chen. 1995. “Asymmetric Synthesis of α-Amino Acids via Chiral N-Alkylidenesulfinamides.” Tetrahedron: Asymmetry 6: 349–352.
  • Lai, S., and D.G. Lee. 2002. “Lewis Acid Assisted Permanganate Oxidations.” Tetrahedron 58: 9879–9888.
  • Leca, D., L. Fensterbank, E. Lacote, and M. Malacria. 2002. “A New Practical One-Pot Access to Sulfonimidates.” Organic Letters 4: 4093–4095.
  • Liu, G., D.A. Cogan, and J.A. Ellman. 1997. “Catalytic Asymmetric Synthesis of tert-Butanesulfinamide. Application to the Asymmetric Synthesis of Amines.” Journal of the American Chemical Society 119: 9913–9914.
  • Liu, G., D.A. Cogan, T.D. Owens, T.P. Tang, and J.A. Ellman. 1999. “Synthesis of Enantiomerically Pure N-tert-Butanesulfinyl Imines (tert-Butanesulfinimines) by the Direct Condensation of tert-Butanesulfinamide with Aldehydes and Ketones.” Journal of Organic Chemistry 64: 1278–1284.
  • Lucas, H.R., L. Li, A.A.N. Sarjeant, M.A. Vance, E.I. Solomon, and K.D. Karlin. 2009. “Toluene and Ethylbenzene Aliphatic C−H Bond Oxidations Initiated by a Dicopper(II)-μ-1,2-Peroxo Complex.” Journal of the American Chemical Society 131: 3230–3245.
  • Maji, M.S., R. Froehlich, and A. Studer. 2008. “Desymmetrization of Metallated Cyclohexadienes with Chiral N-tert-butanesulfinyl Imines.” Organic Letters 10: 1847–1850.
  • Monika, A.-J., and K.R.S. Aneta. 2007. “A Facile Synthesis of N-Sulfinylaldimines.” Tetrahedron: Asymmetry 18: 2507–2509.
  • Morales, S., F.G. Guijarro, R.J.L. Garcia, and M.B. Cid. 2014. “A General Aminocatalytic Method for the Synthesis of Aldimines.” Journal of the American Chemical Society 136: 1082–1089.
  • Mukade, T., D.R. Dragoli, and J.A. Ellman. 2003. “Parallel Solution-Phase Asymmetric Synthesis of α-Branched Amines.” Journal of Combinatorial Chemistry 5: 590–596.
  • Nicolaou, K.C., P.S. Baran, and Y.L. Zhong. 2001. “Selective Oxidation at Carbon Adjacent to Aromatic Systems with IBX.” Journal of the American Chemical Society 123: 3183–3185.
  • Robak, M.A.T., M.A. Herbage, and J.A. Ellman. 2010. “Synthesis and Applications of tert-Butanesulfinamide.” Chemical Review 110: 3600–3740.
  • Sanaboina, C., S. Jana, and L. Eppakayala. 2014. “Efficient Microwave-Assisted Synthesis of N-(tert-Butylsulfinyl)imines Catalyzed by Amberlist-15.” Synlett 25: 1006–1008.
  • Sarina, S., H. Zhu, Z. Zheng, S. Bottle, J. Chang, X. Ke, J.C. Zhao, Y. Huang, A. Sutrisno, M. Willans, and G. Li. 2012. “Driving Selective Aerobic Oxidation of Alkyl Aromatics by Sunlight on Alcohol Grafted Metal Hydroxides.” Chemical Science 3: 2138–2146.
  • Sun, X., X. Tu, C. Dai, X. Zhang, B. Zhang, and Q. Zeng, 2012. “Palladium-Catalyzed C–N Cross Coupling of Sulfinamides and Aryl Halides.” Journal of Organic Chemistry 77: 4454–4459.
  • Sun, P., S.M. Weinreb, and M. Shang. 1997. “tert-Butylsulfonyl (Bus), a New Protecting Group for Amines.” Journal of Organic Chemistry 62: 8604–8608.
  • Weix, D.J., Y. Shi, and J.A. Ellman. 2005. “Diastereoselective and Enantioselective Rh(I)-Catalyzed Additions of Arylboronic Acids to N-tert-Butanesulfinyl and N-Diphenylphosphinoyl Aldimines.” Journal of the American Chemical Society 127: 1092–1093.
  • Würtele, C., O. Sander, V. Lutz, T. Waitz, F. Tuczek, and S. Schindler. 2009. “Aliphatic C−H Bond Oxidation of Toluene Using Copper Peroxo Complexes That Are Stable at Room Temperature.” Journal of the American Chemical Society 131: 7544–7545.
  • Yoshino, Y., Y. Hayashi, T. Iwahama, S. Sakaguchi, and Y. Ishii. 1997. “Catalytic Oxidation of Alkylbenzenes with Molecular Oxygen under Normal Pressure and Temperature by N-Hydroxyphthalimide Combined with Co(OAc)2.” Journal of Organic Chemistry 62: 6810–6813.
  • Zhou, L.-H., X.-Q. Yu, and L. Pu. 2010. “Na-Promoted Aerobic Oxidation of Alcohols to Ketones.” Tetrahedron Letters 51: 475–477.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.