Rh-catalyzed highly enantioselective formation of functionalized cyclopentanes and cyclopentanones.
A catalyst system, [Rh(COD)Cl](2)-BINAP-AgSbF(6), has been developed as a second-generation catalyst for the cycloisomerization of 1,6-enynes tethered by carbon chains. Cyclopentanes and cyclopentanones, which can contain functional groups, such as the 1,4-dienes, vinyl ether, aldehyde etc., were obtained from readily available starting materials in high yields and selectivities. Both regioselectivities and enantioselectivities are excellent: only 1,4-dienes were observed and in over 99% ee.
Liu
Fei
F
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, P. R. China.
Liu
Qiang
Q
He
Minsheng
M
Zhang
Xumu
X
Lei
Aiwen
A
D000965:Antimony / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
C406943:BINAP, 2-naphthol; D003517:Cyclopentanes; D009281:Naphthalenes; D009942:Organometallic Compounds; C007201:cyclopentanone; D012834:Silver; D000965:Antimony; D012238:Rhodium