Abstract
The diastereoselectivity of Ireland-Claisen rearrangements of allylic glycolates is dependent on the E:Z ratio of the silyl ketene acetals, the alkene geometry in the allyl unit, and the transition state topography. High yields and excellent diastereoselectivities (>95:5) have been achieved for selected substrates, including those with R 2 = ethyl that results in a newly formed quaternary center. A discussion of the scope, selectivities, and transition state models will be presented.
Original language | English (US) |
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Pages (from-to) | 825-828 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 53 |
Issue number | 7 |
DOIs | |
State | Published - Feb 15 2012 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry