Asymmetric synthesis of β-substituted γ-lactams via rhodium/diene-catalyzed 1,4-additions: application to the synthesis of (R)-baclofen and (R)-rolipram.
An efficient rhodium/diene-catalyzed asymmetric addition of arylboronic acids to α,β-unsaturated γ-lactams has been developed. The power of this methodology is further demonstrated by the concise synthesis of (R)-baclofen and (R)-rolipram.
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Cheng
C
Shao
Hong-Jie
HJ
Yu
Nuo-Yi
NY
Wu
Ping
P
Tian
Rui
R
Wang
Chen-Guo
CG
Feng
Guo-Qiang
GQ
Lin
D001418:Baclofen / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D020889:Rolipram / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
D001897:Boronic Acids; D047090:beta-Lactams; D012238:Rhodium; D001418:Baclofen; D020889:Rolipram