Abstract
(Chemical Equation Presented) Both syn- and anti-1,2-diols can be obtained with high diastereoselectivity and enantioselectivity from the properly substituted glycolate-derived silyl ketene acetals in the presence of SiCl 4 and a chiral bisphosphoramide catalyst (see scheme; TMS=trimethylsilyl, TBS=tert-butyldimethylsilyl). The sense of diastereoselectivity can be reversed by changing the size of the substituents on the silyl ketene acetals.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1890-1892 |
| Number of pages | 3 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 47 |
| Issue number | 10 |
| DOIs | |
| State | Published - Feb 22 2008 |
Keywords
- 1,2-diols
- Aldol reaction
- Diastereoselectivity
- Enantioselectivity
- Lewis base catalysis
ASJC Scopus subject areas
- Catalysis
- General Chemistry