Effective Procedure for Selective Ammonolysis of Monosubstituted Oxiranes: Application to E7389 Synthesis.
A highly effective procedure is reported to synthesize 1,2-aminoalcohols by regio- and chemo-selective ammonolysis of monosubstituted epoxides. Additive- and concentration-effects were studied, revealing that: (1) methanesulfonic acid is most effective among the additives tested and (2) formation of bis-adducts is practically eliminated at [C] </= 40 mM. The optimum condition thus identified was successfully applied to the final step of the synthesis of potent anti-tumor compound E7389.
Kaburagi
Yosuke
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Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Kishi
Yoshito
Y