Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam
نویسندگان
چکیده
منابع مشابه
Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam
The first synthesis of α-(trifluoromethyl)-β-lactam ((S)-1) is reported. The route starts from α-(trifluoromethyl)acrylic acid (2). Conjugate addition of α-(p-methoxyphenyl)ethylamine ((S)-3b), generated an addition adduct 4b which was cyclised to β-lactam 5b. Separation of the diastereoisomers by chromatography gave ((αS,3S)-5b). N-Debenzylation afforded the desired α-(trifluoromethyl)-β-lacta...
متن کاملDiastereoselective synthesis of potent antimalarial cis-β-lactam agents
Fifteen novel β-lactams bearing the N-ethyl tert-butyl carbamate group 5a-o and fifteen N-(2-aminoethyl) β-lactams 6a-o were synthesized by the ketene-imine [2+2] cycloaddition reaction (Staudinger ). The cycloaddition reaction was found to be totally diastereoselective leading exclusively to the formation of the cis-β-lactam derivatives. These newly synthesized β-lactams were evaluated for the...
متن کاملSynthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives.
A comprehensive survey of pathways leading to the generation of α-trifluoromethyl monocyclic piperidinic derivatives is provided (65 references). These compounds have been synthesized either from 6-membered rings e.g., pipecolic acid or lactam derivatives by introduction a trifluoromethyl group, from pyridine or pyridinone derivatives by reduction, and from 5-membered rings e.g., prolinol deriv...
متن کاملDiastereoselective synthesis of potent antimalarial cis-β-lactam agents
Fifteen novel β-lactams bearing the N-ethyl tert-butyl carbamate group 5a-o and fifteen N-(2-aminoethyl) β-lactams 6a-o were synthesized by the ketene-imine [2+2] cycloaddition reaction (Staudinger ). The cycloaddition reaction was found to be totally diastereoselective leading exclusively to the formation of the cis-β-lactam derivatives. These newly synthesized β-lactams were evaluated for the...
متن کاملCatalytic asymmetric conjugate addition of terminal alkynes to β-trifluoromethyl α,β-enones.
The first enantioselective conjugate alkynylation of β-trifluoromethyl α,β-enones using terminal alkynes and a taniaphos-Cu(I) complex as catalyst is described. Ketones bearing a trifluoromethylated propargylic chiral centre in the β-position were obtained with good yields and high enantiomeric excesses (up to 99%).
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Beilstein Journal of Organic Chemistry
سال: 2011
ISSN: 1860-5397
DOI: 10.3762/bjoc.7.86