Asymmetric reduction of perfluoroalkyl ketones with chiral lithium alkoxides

Tetrahedron Letters

Volumn 47, Issue 16, 2006, Pages 2821-2824

  Sokeirik, Yasser Samir ^a   Sato, Kazuyuki ^a   Omote, Masaaki ^a   Ando, Akira ^a   Kumadaki, Itsumaro ^a  

^a SETSUNAN UNIVERSITY   (Japan)

Author keywords

(Perfluoroalkyl)carbinol; 1 Phenylethanol; Asymmetric reduction; Chiral transfer; Lithium alkoxide; Perfluoroalkyl ketone; Steric effect; Trifluoroacetophenone

Indexed keywords

1 PHENYLETHOXIDE; 1H 1 PHENYLPERFLUOTOOCTANOL; 2,2,2 TRIFLUORO 1 PHENYLETHANOL; 2,2,2, TRIFLUOROACETOPHENONE; ACETOPHENONE DERIVATIVE; ALCOHOL DERIVATIVE; ALPHA PERFLUOROALKYL ALCOHOL DERIVATIVE; KETONE DERIVATIVE; LITHIUM ALKOXIDE DERIVATIVE; OCTANE; OCTANOL; OXIDE; PERFLUOROALKYL KETONE DERIVATIVE; PERFLUOROOCTAN 1 ONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; REDUCTION;

TRIFLUORO;

EID: 33644992892     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.078     Document Type: Article

References (9)

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2. M. Omote, Y. Nishimura, K. Sato, A. Ando, and I. Kumadaki Tetrahedron Lett. 46 2005 319 322
3. M. Omote, Y. Nishimura, K. Sato, A. Ando, and I. Kumadaki J. Fluorine Chem. 126 2005 407 409
4. Y.S. Sokeirik, K. Sato, A. Ando, and I. Kumadaki J. Fluorine Chem. 127 2006 150 152
5. D. Nasipuri, and P.K. Bhattacharya J. Chem. Soc., Perkin Trans. 1 1977 576 578
6. Compound 3 is commercially available.
7. 2O in hexane) to give 10 (134 mg, 68%) as a yellow oil.
8. D for (S)-isomer is +23.2. V. Ramachandran, A. Teodorvic, and H.C. Brown Tetrahedron 49 1993 1725 1738
9. 2O in hexane) to remove coloring material and analyzed with GC without further purification to compare the retention time with compound 8 (nonchiral column, temp 80-200°C/min). Retention time: sample from chiral reduction with Li alkoxide; 4.296 min. Sample from diazotization: 4.303. Chiral column temp 150°C. The former sample: minor peak; 6.963 min, major peak; 7.240 min. The latter sample: minor peak; 6.940, major peak; 7.246 minor peak; 7.246 min.