Synthesis of enantiomerically pure functionalised amides (EPC-synthesis) from chiral β-aminated organolithium intermediates
1994; Elsevier BV; Volume: 35; Issue: 27 Linguagem: Inglês
10.1016/s0040-4039(00)76980-2
ISSN1873-3581
AutoresFrancisco Foubelo, Miguel Yus,
Tópico(s)Advanced Synthetic Organic Chemistry
ResumoThe successive deprotonation-lithiation of chiral chloroamides 1 with n-butyllithium and lithium naphthalenide, respectively, at −78°C leads to the corresponding chiral β-aminated organolithium intermediates 2, which by reaction with different electrophiles [H2O, D2O, Me2S2, (CH2)5CO, ButCHO and PhCHO] yield, after hydrolysis, the corresponding enantiomerically pure compounds 3. In the case of using aldehydes as electrophilic reagents, a mixture of diastereomers are obtained, which are easily separated by flash chromatography, so enantiomerically pure 1,3-aminoalcohol derivatives are accessible by this procedure.
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