Asymmetric synthesis of both enantiomers of anti-4,4,4-trifluorothreonine and 2-amino-4,4,4-trifluorobutanoic acid.
A short and efficient enantioselective synthesis of both enantiomers of anti-4,4,4-trifluorothreonine and 2-amino-4,4,4-trifluorobutanoic acid was successfully developed. Trifluoromethylation of benzyl-protected bromoalkene 4 provided key intermediate trifluoromethylated trans-disubstituted alkene 2 in good yield. The sequence then involved Sharpless asymmetric dihydroxylation, nucleophilic opening of cyclic sulfate with NaN(3), palladium-catalyzed selective hydrogenation, and oxidation.
Jiang
Zhong-Xing
ZX
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 354 Fenglin Lu, Shanghai 200032, China.
Qin
Ying-Ying
YY
Qing
Feng-Ling
FL
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002087:Butyrates / Q000138:chemical synthesis*; D002626:Chemistry, Pharmaceutical; D005461:Fluorine; D006845:Hydrocarbons, Fluorinated; D013237:Stereoisomerism; D013912:Threonine / Q000031:analogs & derivatives / Q000138:chemical synthesis*
C482353:2-amino-4,4,4-trifluorobutanoic acid; D000596:Amino Acids; D002087:Butyrates; D006845:Hydrocarbons, Fluorinated; C482352:anti-4,4,4-trifluorothreonine; D005461:Fluorine; D013912:Threonine