Short and practical synthesis of O-(p-biphenoyl)-N-tosyl-allo-threonine-derived oxazaborolidinone catalyst |
| |
| Authors: | Harada Toshiro Inui Chieko |
| |
| Institution: | Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. harada@chem.kit.ac.jp |
| |
| Abstract: | O-(p-Biphenoyl)-N-tosyl-(L)-allo-threonine methyl ester is synthesized in three steps (65% overall yield) starting from commercially available (L)-allo-threonine methyl ester hydrochloride by N-acylation followed by N,O-acyl migration with inversion of the beta carbinol carbon and N-tosylation. Treatment of the methyl ester with dibromophenylborane gives oxazaborolidinone 1, which can be used as a Lewis acid catalyst for the asymmetric Michael and Diels-Alder reactions. |
| |
| Keywords: | |
| 本文献已被 PubMed 等数据库收录！ |
|
