Aminative umpolung of aldehydes to α-amino anion equivalents for Pd-catalyzed allylation: an efficient synthesis of homoallylic amines.
An attractive strategy for generation of α-amino anions from aldehydes with applications in synthesis of homoallylic amines is described. Aromatic aldehydes can be converted to α-amino anion equivalents via amination with 2,2-diphenylglycine and subsequent decarboxylation. The in situ generated α-imino anions are highly reactive for Pd-catalyzed allylation, forming the corresponding homoallylic amines in high yields with excellent regioselectivity.
The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Lab of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, China.
Lei
L
Ding
Jing
J
Chen
Yifan
Y
Hu
Juan
J
Xu
Xing
X
Gong
Dongfang
D
Xu
Baoguo
B
Zhao
Hexing
H
Li
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000838:Anions / Q000737:chemistry*; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines; D000838:Anions; D010165:Palladium; D005998:Glycine