Stereodivergent construction of aminodiols with a CF3 group

Organic Letters

Volumn 12, Issue 19, 2010, Pages 4316-4319

  Obinata, Ryusuke ^a   Kawasaki Takasuka, Tomoko ^a   Yamazaki, Takashi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957149164     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101459a     Document Type: Article

References (14)

1. Yamazaki, T.; Taguchi, T.; Ojima, I. In Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed.; John Wiley & Sons: New York, 2009; p 3.
2. Bégué, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley: Hoboken, NJ, 2008.
3. OHagan, D.; Harper, D. B. J. Fluorine Chem. 1999, 100, 127-133
4. Uneyama, K. Organofluorine Chemistry; Blackwell Publishing: Oxford, 2006.
5. Yamazaki, T.; Ichige, T.; Kitazume, T. Org. Lett. 2004, 6, 4073-4076
6. Hanson, R. M. Org. React. 2002, 60, 1-15
7. Because the DIBAL reduction of 1a (R = Ph) was found to proceed in an irregularly anti -selective manner (61% anti), the product, E-syn-2a was not used throughout this work.
8. Smart, B. E. J. Fluorine Chem. 2001, 109, 3-11
9. The same 3-amino-1,2-diol selectivity was also confirmed by E-anti-2b and-3b.
10. 1H NMR. The coupling pattern of the shifted proton (dd, not d) led to an unambiguous conclusion that the product was anti, anti-4a. For the detailed experimental procedure and spectroscopic data, see the Supporting Information.
11. Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887. Because the β value for the hydrogen-bonding accepting ability of n -propanol was missing, the values of ethanol and n -butanol were referred to for the discussion
12. Yamazaki, T.; Iwatsubo, H.; Kitazume, T. Tetrahedron: Asymmetry 1994, 5, 1823-1830
13. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736
14. Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736-738