1026535-64-7Relevant academic research and scientific papers
A synthesis of α-lithiated enol ethers from α-arenesulfinyl enol ethers: Ni(0)- and Pd(0)-catalysed coupling of enol triflates and phosphates derived from lactones with sodium arenethiolates gives α-arenesulfanyl enol ethers
Milne, Jacqueline E.,Kocienski, Philip J.
, p. 584 - 592 (2007/10/03)
A three-step synthesis of stable and storable α-benzene-sulfinyl enol ethers from lactones entails (a) conversion of a lactone to an enol triflate or phosphate; (b) Ni(0) and Pd(0) cross-coupling of the enol triflate or phosphate with a sodium arenethiolate to give an α-arenethio enol ether; and (c) oxidation of an arenethio group to a sulfoxide. The α-benzenesulfinyl enol ethers undergo sulfoxide-lithium exchange on reaction with n-BuLi to give α-lithiated enol ethers thus making the α-benzenesulfinyl group a surrogate for the trialkylstannyl group which has hitherto served as the most common precursor to α-lithiated enol ethers.
The preparation of 6-bromo-3,4-dihydro-2H-pyrans from tetrahydropyran-2-ones via a Ni(0)-catalysed coupling reaction and their halogen-metal exchange to 6-lithio-3,4-dihydro-2H-pyrans
Milne, Jacqueline E.,Jarowicki, Krzysztof,Kocienski, Philip J.
, p. 607 - 609 (2007/10/03)
The enol triflate derivatives prepared from readily accessible tetrahydropyran-2-ones undergo Ni(0)-catalysed substitution with LiBr to give the corresponding 6-bromo-3,4-dihydro-2H-pyrans under mild conditions. The 6-bromo-3,4-dihydro-2H-pyrans undergo h
A synthesis of 6-tributylstannyl-3,4-dihydro-2H-pyrans via coupling of enol triflates with (Bu3Sn)(Bu)Culi·liCN
Wildman, Tanya,Kocienski, Philip J.,Narquizian, Robert,Whittingham, William G.
, p. 393 - 398 (2007/10/03)
Enol triflates derived from 6- and 7-membered ring lactones (6 cases) react with (Bu3Sn)(Bu)CuLi·LiCN in THF at -78 °C to give the corresponding α-tributylstannyl cyclic enol ethers in 54-85% yield.
