New chiral hypervalent iodine compounds in asymmetric synthesis

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 7674-7679

  Hirt, Urs H ^a   Spingler, Bernhard ^a   Wirth, Thomas ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001082990     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980475x     Document Type: Article

References (39)

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32. The absolute configuration was determined by comparison with (S)-4, which was synthesized from (S)-mandelic acid by reduction and tosylation: Dale, J. A.; Mosher, H. S. J. Org. Chem. 1970, 35, 40024003.
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34. The enantiomeric excess was determined by HPLC: Chiralcel OD; 9:1 hexane/2-propanol; 0.5 mL/min; 254 nm.
35. The enantiomeric excess was determined by HPLC: Chiralcel OB; 4:1 hexane/2-propanol, 0.5 mL/miri; 240 nm.
36. The enantiomeric excess was determined by GC: Chrompack, 0-CD-permethylated; 25 m, 80 -140 °C; 5 °C/min.
37. The enantiomeric excess was determined by HPLC: Chiralcel OD; 9:1 hexane/2-propanol, 0.5 mlVmin; 220 nm.
38. The configuration is determined by reduction of 13a with LiAlHi to (S)-l-(4-methoxyphenyl)ethanol and comparison of the optical rotation with the literature: Brown, S. M.; Davies, S. G.; Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813-822.
39. The configuration is determined by reduction of 13b with LiAlHi to (S)-l-(3-methoxyphenyl)ethanol and comparison of the optical rotation with the literature: Chen, C. P.; Prasad, K.; Repic, O. Tetrahedron Lett. 1991, 32, 7175-7178.