Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free NH group for the synthesis of beta-amino acid derivatives.
We describe highly enantioselective synthesis of beta-amino acid derivatives (1a-c) using asymmetric hydrogenation of alpha-aminomethylacrylates (2a-c), which contain a free basic N H group, as the key step. The alpha-aminomethylacrylates (2a-c) were prepared using the Baylis-Hillman reaction of an appropriate aldehyde with methyl acrylate followed by acetylation of the resulting allylic alcohols (4a-b) and S(N)2'-type amination of the allylic acetates (3a-b).
Qiu
Liqin
L
Process Research and Development, Chemical and Analytical Development, Novartis Pharmaceuticals Corporation, One Health Plaza, East Hanover, NJ 07936, USA.
Prashad
Mahavir
M
Hu
Bin
B
Prasad
Kapa
K
Repic
Oljan
O
Blacklock
Thomas J
TJ
Kwong
Fuk Yee
FY
Kok
Stanton H L
SH
Lee
Hang Wai
HW
Chan
Albert S C
AS
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D006865:Hydrogenation; D008689:Methacrylates / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D008689:Methacrylates