Synthesis 2018; 50(17): 3322-3332
DOI: 10.1055/s-0037-1610214
feature
© Georg Thieme Verlag Stuttgart · New York

Oxidative Kinetic Resolution of Some Naphtholic Alcohols Mediated by a Chiral Hypervalent Iodine Reagent

Nikita Jain
Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada   Email: ciufi@chem.ubc.ca
,
Marco A. Ciufolini*
Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada   Email: ciufi@chem.ubc.ca
› Author Affiliations
We thank NSERC for support of this research.
Further Information

Publication History

Received: 22 May 2018

Accepted after revision: 21 June 2018

Publication Date:
02 August 2018 (eFirst)

Abstract

A chiral aryl iodide enables the catalytic, oxidative kinetic resolution of various 2-[(3-hydroxy-2-alkyl)propyl]naphthalen-1-ols.

Supporting Information

 
  • References

  • 1 Jain N. Xu S. Ciufolini MA. Chem. Eur. J. 2017; 23: 4542
  • 3 For an excellent bibliography of chiral iodides as promoters of enantioselective reactions see: Fujita M. Heterocycles 2018; 96: 563 ; and literature cited therein
    • 4a Uyanik M. Yasui T. Ishihara K. Angew. Chem. Int. Ed. 2010; 49: 2175
    • 4b Uyanik M. Yasui T. Ishihara K. Angew. Chem. Int. Ed. 2013; 52: 9215
    • 4c Uyanik M. Yasui T. Ishihara K. J. Org. Chem. 2017; 82: 11946
    • 5a Beesley RM. Ingold CK. Thorpe JF. J. Chem. Soc., Trans. 1915; 107: 1080
    • 5b Bachrach SM. J. Org. Chem. 2008; 73: 2466
  • 6 This would be an example of oxidative kinetic resolution; for review, see: Keith JM. Larrow JF. Jacobsen EN. Adv. Synth. Catal. 2001; 343: 5 ; (see esp. 11 ff)

    • To illustrate:
    • 7a Oxidative kinetic resolution of rac-1-phenylethanol: Zhdankin VV. Koposov AY. Netzel BC. Yashin NV. Rempel BP. Ferguson MJ. Tykwinski RR. Angew. Chem. Int. Ed. 2003; 42: 2194 ; (see especially p 2195, paragraph above Table 1)
    • 7b Oxidative kinetic resolution of rac-1-(2-naphthyl)ethanol and meso-1,2-diphenylethane-1,2-diol: Ladziata U. Carlson J. Zhdankin VV. Tetrahedon Lett. 2006; 47: 6301
    • 7c Kinetic resolution of a secondary homoallyl alcohol via oxidative lactonization: Fujita M. Mori K. Shimogaki M. Sugimura T. Org. Lett. 2012; 14: 1294
    • 7d We thank the referees for bringing the above literature to our attention.
  • 8 See Supporting Information for relevant synthetic, chemical, and spectroscopic data, and other characterization details.
  • 9 Fluoroalcohols such as CF3CH2OH and (CF3)2CHOH are privileged media for the conduct of many reactions mediated by hypervalent iodine species: Dohi T. Yamaoka N. Kita Y. Tetrahedron 2010; 66: 5775
    • 10a Terakado D. Koutaka H. Oriyama T. Tetrahedron: Asymmetry 2005; 16: 1157
    • 10b Sakai T. Kishimoto T. Tanaka Y. Ema T. Utaka M. Tetrahedron Lett. 1998; 39: 7881
    • 10c Ghanemi A. Aboul-enein HY. Chirality 2005; 17: 1
    • 10d Strübing D. Krumlinde P. Piera J. Bäckvall J.-E. Adv. Synth. Catal. 2007; 349: 1577
  • 11 Racemic 1n is a known compound: Kongkathip N. Kongkathip B. Siripong P. Sangma C. Luangkamin S. Niyomdecha M. Pattanapa S. Piyaviriyagul S. Kongsaeree P. Bioorg. Med. Chem. 2003; 11: 3179