Direct generation of Ti-enolate of α-CF3 ketone: Theoretical study and high-yielding and diastereoselective aldol reaction

Journal of the American Chemical Society

Volumn 126, Issue 41, 2004, Pages 13174-13175

  Itoh, Yoshimitsu ^a   Yamanaka, Masahiro ^a,b   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b RIKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROCARBON; KETONE; LITHIUM; TITANIUM DERIVATIVE; TITANIUM TETRACHLORIDE;

ALDOL REACTION; ARTICLE; CHEMICAL BOND; CRYSTALLOGRAPHY; DEFLUORINATION; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY ANALYSIS;

ALDEHYDES; HYDROCARBONS, FLUORINATED; KETONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; THERMODYNAMICS; TITANIUM;

EID: 6044260122     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046518a     Document Type: Article

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36. X-ray structure of the product with benzaldehyde was obtained. CCDC 240382 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via the Internet at www.ccd-c.cam.ac.uk/ data_request/cif, by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
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41. In sharp contrast, in the case with fluoral, the anti diastereoselectivity did not change (anti:syn = 62:38) even in the presence of HMPA. This could be the evidence for the dipole interaction-controlled diastereoselectivity in the case of fluoral. See ref 13.