Asymmetric Lewis acid mediated [1,2]-rearrangement of proline-derived ammonium ylides.
The first example of asymmetric Lewis acid mediated [1,2]-rearrangement of N-benzylic proline amides to form quaternary proline derivatives is reported. The presented reaction is shown to proceed with remarkable high C-->N-->C chirality transfer. Various quaternary proline derivatives have been prepared in good to excellent yields and high enantiomeric purity.
Tuzina
Pavel
P
Organic Chemistry, KTH Chemical Science and Engineering, SE-100 44 Stockholm, Sweden.
Somfai
Peter
P
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011392:Proline