Base-accelerated enantioselective substitution of Morita-Baylis-Hillman carbonates with dialkyl phosphine oxides.
A base could accelerate the S(N)2' or S(N)2'-S(N)2' reaction of Morita-Baylis-Hillman (MBH) carbonates with dialkyl phosphine oxides, but the judicial choice of an appropriate base would greatly depress this competitive S(N)2' reaction and allow for a highly enantioselective allylic substitution reaction with satisfactory yields and excellent enantioselectivities.
Sun
Wangsheng
W
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, China.
Hong
Liang
L
Liu
Chunxia
C
Wang
Rui
R
D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010087:Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D010720:Phosphines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002254:Carbonates; D010087:Oxides; D010720:Phosphines; C044646:phosphine