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Catalytic Asymmetric Cascade Vinylogous Mukaiyama 1,6-Michael/Michael Addition of 2-Silyloxyfurans with Azoalkenes: Direct Approach to Fused Butyrolactones.
- Source :
-
Journal of the American Chemical Society . 8/19/2015, Vol. 137 Issue 32, p10124-10127. 4p. - Publication Year :
- 2015
-
Abstract
- An unprecedented cascade vinylogous Mukaiyama 1,6-MA/MA of 2-silyloxyfurans and azoalkenes was realized with a Cu(II)/tBu-Box complex. An array of fused butyrolactones containing multiple stereocenters was generally obtained in good yield (up to 90% yield) with exclusive diastereoselectivity (>20:1 dr) and excellent enantioselectivity (up to 99% ee). Carbon isotope effects measured by 13C NMR revealed a stepwise mechanism for this annulation process. [ABSTRACT FROM AUTHOR]
- Subjects :
- *LACTONES
*ANNULATION
*CARBON isotopes
*KINETIC isotope effects
*CHEMICAL reactions
Subjects
Details
- Language :
- English
- ISSN :
- 00027863
- Volume :
- 137
- Issue :
- 32
- Database :
- Academic Search Index
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 109259481
- Full Text :
- https://doi.org/10.1021/jacs.5b06509