✦ LIBER ✦
α-Lithiation-rearrangement of N-toluenesulfonyl aziridines with sec-butyllithium and (−)-sparteine: opposite sense of asymmetric induction to epoxides
✍ Scribed by Peter O'Brien; Clare M Rosser; Darren Caine
- Book ID
- 104254264
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 185 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
The a-lithiation rearrangement of three cyclic N-toluenesulfonyl (tosyl) aziridines has been carried out using sec-butyllithium/(-)-sparteine. In each case, it was established that preferential lithiation of the S-aziridine stereocentre occurred. This is the opposite sense of asymmetric induction to that observed with epoxides.