Highly diastereoselective lithiation (s-BuLi/TMEDA ix Et2O, -78 degrees C, 2 h) of (5)-2-ferroceny1-4-(substituted)-oxazolines followed by addition of MeOH-d(4) gave up to 95% D incorporation. Subsequent application of alternative lithiation conditions (n-BuLi in THF, -78 degrees C, 2 h), followed by addition of an electrophile, resulted in a reversal of diastereoselectivity controlled primarily by the high k(H)/k(D) value for lithiation (isomer ratio typically between 10:1 and 20:1).
|Number of pages||4|
|Early online date||24 Jan 2017|
|Publication status||Published - 3 Feb 2017|
- School of Chemistry - Reader in Organic Chemistry
- Chemistry of Materials and Catalysis - Member
Person: Research Group Member, Academic, Teaching & Research