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Synthesis 2018; 50(17): 3322-3332
DOI: 10.1055/s-0037-1610214
DOI: 10.1055/s-0037-1610214
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Oxidative Kinetic Resolution of Some Naphtholic Alcohols Mediated by a Chiral Hypervalent Iodine Reagent
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 (online)
Abstract
A chiral aryl iodide enables the catalytic, oxidative kinetic resolution of various 2-[(3-hydroxy-2-alkyl)propyl]naphthalen-1-ols.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610214. Preparation and kinetic resolution of alcohols 1a–q; characterization data; 1H and 13C NMR spectra (104 pages).
- Supporting Information
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References
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- 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)
- 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
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- 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
General reviews on hypervalent iodine chemistry:
To illustrate: