Modular Synthesis of Chiral Homo- and Heterotrisoxazolines. Improving the Enantioselectivity in the Asymmetric Michael Addition of Indole to Benzylidene Malonate
- 22 June 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (15) , 6108-6110
- https://doi.org/10.1021/jo050595m
Abstract
A simple approach to a diverse set of chiral trisoxazolines is described. Deprotonation of bisoxazolines 2, followed by treatment of 2-chloromethyloxazolines 3, affords chiral trisoxazolines, including chiral homo- and hetero-trisoxazolines in good to high yields. These trisoxazolines are successfully applied in the asymmetric reaction of indole with benzylidene malonate, and ee's up to 93% were obtained.Keywords
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