摘要

The formal 1,3-dipolar cycloaddition of azomethine ylides and aldehydes is explored, as hydrolysis of the resulting oxazolidine product gives facile access to valuable syn-beta-aryl-beta-hydroxy-alpha-amino esters. The use of using benzaldehyde-derived imines as the ylide precursor results in 1,3-dipolar cycloaddition with high conversions but low diastereoselectivity. In contrast, the employment of benzophenone-derived imines as the ylide precursor results in an aldol reaction, which gives the intermediate oxazolidine in high diastereoselectivity and requires a weak acid catalyst to achieve higher conversions.

  • 出版日期2010-7