Stereospecific synthesis of cis-2-alkoxy-3-aminooxolanes
(1997) The Journal of Organic Chemistry — Vol. 62, n° 15, p. 5138-5143 (1997)
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- Abstract
- cis-2-Alkoxy-3-aminooxolanes 4 were synthesized in a remarkably stereospecific manner by alcoholysis of alpha-chloro-gamma-((trimethylsilyl)oxy)ketimines 2, obtained by alkylation of alpha-chloroketimines 1 with 2-bromo-1-((trimethylsilyl)oxy)ethane. The stereospecificity of the cyclization was lost when the alcoholysis was performed in the presence of base. However, complete transformation of the mixtures of cis- and trans-2-alkoxy-3-aminooxolanes into the more stable cis-compounds was achieved with hydrogen chloride in methanol. A mechanistic rationale for these stereochemical aspects is presented.
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Dekimpe, N., Aelterman, W., DeGeyter, K., & Declercq, J.-P. (1997). Stereospecific synthesis of cis-2-alkoxy-3-aminooxolanes. The Journal of Organic Chemistry, 62(15), 5138-5143. https://doi.org/10.1021/jo970410e (Original work published 1997)