Enantioselective synthesis of beta-iodo Morita-Baylis-Hillman esters by a catalytic asymmetric three-component coupling reaction.
A catalytic route toward chiral Morita-Baylis-Hillman esters by asymmetric coupling between alpha,beta-acetylenic esters, aldehydes, and trimethylsilyl iodide has been developed (see scheme). The reaction proceeds with high to excellent enantioselectivities, and the products can be transformed into beta-branched derivatives in a single step and with excellent retention of configuration. TMS = trimethylsilyl.
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon City, Gyeonggi-do, 440-746, Korea.
Bidyut Kumar
BK
Senapati
Geum-Sook
GS
Hwang
Sungil
S
Lee
Do Hyun
DH
Ryu
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000447:Aldehydes; D004952:Esters; D014297:Trimethylsilyl Compounds; C419804:trimethylsilyl iodide