Effective Procedure for Selective Ammonolysis of Monosubstituted Oxiranes: Application to E7389 Synthesis.

Abstract

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.

• Authors: Yosuke Kaburagi, Yoshito Kishi
• Journal: Tetrahedron letters (Tetrahedron Lett) Vol. 48 Issue 51 Pg. 8967-8971 (Dec 2007) ISSN: 0040-4039 [Print] England
• PMID: 19050739 (Publication Type: Journal Article)