Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates.
The direct asymmetric allylic alkylation of beta,gamma-butenolides with MBH carbonates to access gamma,gamma-disubstituted butenolides containing adjacent quaternary and tertiary chiral centers has been presented in excellent stereoselectivities (86-96% ee, dr >95:5) and moderate to good yield (50-83%). Their synthetic utility has been well demonstrated by the facile construction of bicyclic lactones bearing 4-5 stereogenic centers.
Cui
Hai-Lei
HL
Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, China.
Huang
Ji-Rong
JR
Lei
Jie
J
Wang
Zhao-Feng
ZF
Chen
Shi
S
Wu
Li
L
Chen
Ying-Chun
YC
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D013237:Stereoisomerism
D000498:Allyl Compounds; D002254:Carbonates; D002930:Cinchona Alkaloids; C004511:butenolide; D015107:4-Butyrolactone