Remote asymmetric trifluoromethylation induced by chiral sulfinyl group: synthesis of enantiomerically pure 1-(2-naphthyl)-2,2,2-trifluoroethanol

Authors :: Sugimoto, Hideki
Nakamura, Shuichi
Shibata, Yoshihiro
Shibata, Norio
Toru, Takeshi
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Feb2006, Vol. 47 Issue 8, p1337-1340. 4p.
Publication Year :: 2006
Abstract: Abstract: The reaction of 1-[(2,4,6-triisopropylphenyl)sulfinyl]-2-naphthaldehyde with (trifluoromethyl)trimethylsilane using tetramethylammonium fluoride gave trifluoromethylated compounds in high yield with high diastereoselectivity. Desilylation and subsequent recrystallization yielded the enantiomerically and diastereomerically pure trifluoroethanol, which afforded chiral 1-(2-naphthyl)-2,2,2-trifluoroethanol after removal of the sulfinyl group. [Copyright &y& Elsevier]

Subjects :: *ORGANIC compounds
*BIOACTIVE compounds
*NUCLEAR isomers
*CARBON compounds

Language :: English
ISSN :: 00404039
Volume :: 47
Issue :: 8
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 19464877
Full Text :: https://doi.org/10.1016/j.tetlet.2005.12.061

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