849693-89-6Relevant academic research and scientific papers
Bis(2-t-butylphenyl)phosphonoacetamides for the highly cis-selective synthesis of α,β-unsaturated amides
Ando, Kaori,Nagaya, Shigeo,Tarumi, Yuko
scheme or table, p. 5689 - 5691 (2011/02/26)
New Horner-Wadsworth-Emmons reagents, (o-t-BuPhO)2P(O)CH2CONMe(OMe) and (o-t-BuPhO)2P(O)CH2CON(CH2CH2) 2O were prepared via the Arbuzov reaction in good yields. The HWE reaction
Application of organocerium reagents for the efficient conversion of Z-α,β-unsaturated Weinreb amides to Z-α,β-unsaturated ketones
Kojima, Satoshi,Hidaka, Tsugihiko,Yamakawa, Atsushi
, p. 470 - 471 (2007/10/03)
The reactions of Z-rich unsaturated Weinreb amides with organolithium and organocerium reagents were examined. Taking in consideration both the extent of geometry retention and cleanness of the reaction, organocerium reagents were more effective for the conversion to Z-α,β-unsaturated ketones. Copyright
Synthesis of β-monosubstituted α,β-unsaturated amides with z-selectivity using diphenylphosphonoacetamides
Kojima, Satoshi,Hidaka, Tsugihiko,Ohba, Yuko
, p. 515 - 523 (2007/10/03)
The utility of diphenylphosphonoacetamides [(PhO)2P(O)CH 2CONRR′] as Horner-Wadsworth-Emmons reagents was examined with five different patterns of substitution upon the amide nitrogen atom (2a: R, R′ = CH2Ph; 2b: R = CH2Ph, R′ = H; 2c: R = Me, R′ = OMe; 2d: R, R′ = Ph; 2e: R, R′ = (CH2) 4). The reaction of 2a was found to be Z-selective for aromatic aldehydes with selectivities up to 95:5. Reagent 2b led to reasonable selectivity for both benzaldehyde (85:15) and 3-phenylpropionaldehyde (87:13), while 2c was somewhat effective for only the latter alkyl aldehyde (83:17). Compounds 2d and 2e exhibited slightly lower selectivities compared with 2a.
