We are very grateful to Dr. Hiroki Akutsu and Prof. Shin′ichi Nakatsuji (Hyogo) for X-ray crystallographic analyses and to Prof. Tadashi Okuyama (Hyogo) for reading this manuscript.
Enantiodifferentiating endo-Selective Oxylactonization of ortho-Alk-1-enylbenzoate with a Lactate-Derived Aryl-λ3-Iodane†
Article first published online: 18 AUG 2010
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 49, Issue 39, pages 7068–7071, September 17, 2010
How to Cite
Fujita, M., Yoshida, Y., Miyata, K., Wakisaka, A. and Sugimura, T. (2010), Enantiodifferentiating endo-Selective Oxylactonization of ortho-Alk-1-enylbenzoate with a Lactate-Derived Aryl-λ3-Iodane. Angew. Chem. Int. Ed., 49: 7068–7071. doi: 10.1002/anie.201003503
- Issue published online: 14 SEP 2010
- Article first published online: 18 AUG 2010
- Manuscript Received: 9 JUN 2010
- asymmetric synthesis;
- hypervalent compounds;
It's the hype: The asymmetric synthesis of 3-alkyl-4-oxyisochroman-1-one is achieved by oxylactonization of ortho-alk-1-enylbenzoate with a series of optically active hypervalent iodine(III) reagents prepared from lactate or valine as a chiral source (see scheme). The oxylactonization is highly regio-, diastereo-, and enantioselective.