Double axial chirality promoted asymmetric [2,3] Stevens rearrangement of N-cinnamyl L-alanine amide-derived ammonium ylides.
The base-induced asymmetric [2,3] Stevens rearrangement of N-cinnamyl tetraalkylammonium ylides derived from L-alanine amides proceeds via a double axially chiral intermediate to afford the corresponding α-substituted alanine derivatives with high enantio- and diastereoselectivities.
Department of Chemistry, Faculty of Science, Niigata University, Niigata, 950-2181, Japan. tayama@chem.sc.niigata-u.ac.jp.
Eiji
E
Tayama
Noriko
N
Naganuma
Hajime
H
Iwamoto
Eietsu
E
Hasegawa
D000409:Alanine / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D064751:Ammonium Compounds / Q000737:chemistry*; D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000577:Amides; D064751:Ammonium Compounds; D000409:Alanine