Ch. Sutton et al., BORON ANALOGS OF VALINE, LEUCINE, AND ISOLEUCINE - SYNTHESIS OF AMINE-ALKYL(C-ALKOXYCARBONYL)BORANES AND AMINE-ALKYL(N,N-DIETHYLCARBAMOYL)BORANES, Inorganic chemistry, 33(19), 1994, pp. 4221-4225
Alkylation of amine-alkyl(C-allcoxy-N-ethylcyano)borane with Et(3)OBF(
4) resulted in the isolation of amine-alkyl(C-alkoxy-N,N-diethyrcyano)
borane tetrafluoroborates, which, upon aqueous base hydrolysis, yielde
d both the amine-alkyl(C-alkoxycarbonyl)borane and the amine-alkyl(N,N
-diethylcarbamoyl)borane in varyng ratios. Amine-alkyl(C-alkoxycarbony
l)boranes (amine = quinuclidine, pyridine; alkyl = iBu, iPr, sBu; alko
xy R = Me, benzyl) representative of several amino acid analogues have
been isolated and characterized. These are the first ester derivative
s of a boron analog other than glycine.