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Dinuclear zinc synergistic catalytic asymmetric phospha-Michael/Michael cascade reaction: synthesis of 1,2,3-trisubstituted indanes bearing phosphoryl groups.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2019 Apr 24; Vol. 17 (17), pp. 4301-4310. - Publication Year :
- 2019
-
Abstract
- A new dinuclear zinc synergistic catalytic asymmetric phospha-Michael/Michael cascade reaction of o-dienones and dialkyl phosphates is reported. This method has been proven to be general and efficient for the formation of a range of chiral 1,2,3-trisubstituted indane compounds containing phosphorus groups in good yields (up to 92%) with excellent stereoselectivities (up to >99% ee and up to >99 : 1 dr). The relative configuration of the product was identified as having a trans,trans substitution pattern via two-dimensional (2D) nuclear Overhauser effect spectroscopy 1H-1H NMR experiments. A possible mechanism was proposed.
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 17
- Issue :
- 17
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 30969299
- Full Text :
- https://doi.org/10.1039/c9ob00544g