111752-63-7Relevant academic research and scientific papers
Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner-Emmons Reagents, Ethyl (Diarylphosphono)acetates
Ando, Kaori
, p. 1934 - 1939 (1997)
New Horner-Emmons reagents, ethyl (diarylphosphono)acetates 1, were prepared from triethyl phosphonoacetate, PCl5 the corresponding phenols. The reaction of 1 with several kinds of aldehydes in the presence of Triton B or NaH in THF solvent revealed that these reagents are useful for the synthesis of Z-unsaturated esters. Among the reagents examined, ethyl(di-o-tolylphosphono)-, [bis(o-ethylphenyl)phosphonol-, and [bis(o-isopropylphenyl)phosphono]acetates (1k-m) were found to be the most effective, giving Z-unsaturated esters with 93-99% selectivity.
Solvent-free Horner-Wadsworth-Emmons reaction using DBU
Ando, Kaori,Yamada, Kyohei
, p. 3297 - 3299 (2010)
The solvent-free Horner-Wadsworth-Emmons reaction with a variety of aldehydes using 1.5 equiv of DBU gave E-α,β-unsaturated esters and ketones in high yields. The E-selectivity was high and the used DBU was recovered.
Highly E-selective solvent-free Horner-Wadsworth-Emmons reaction catalyzed by DBU
Ando, Kaori,Yamada, Kyohei
supporting information; experimental part, p. 1143 - 1146 (2011/06/24)
The solvent-free Horner-Wadsworth-Emmons reaction of triethyl phosphonoacetate with a variety of aldehydes was catalyzed by DBU in the presence of K2CO3 to give E-α,β-unsaturated esters highly selectively (99:1 for most of the reactions). The reaction with ketones gave trisubstituted olefins with good to high E-selectivity by DBU-Cs2CO3.
Stereoselective Radical Additions of γ-Oxy-α,β-unsaturated Ester Derivatives; 1,2-Asymmetric Induction in Acyclic and Cyclisation Systems
Morikawa, Tsutomu,Washio, Yoshiaki,Harada, Susumu,Hanai, Ryo,Kayashita, Takashi,et al.
, p. 271 - 282 (2007/10/02)
Examination was made of 1,2-asymmetric induction in the addition of alkyl radicals to γ-oxy-α,β-unsaturated ester derivatives 1 and 2 prepared from ethyl lactate and (R)-2,3-O-isopropylideneglyceraldehyde 3, respectively.The addition reactions of hexyl, cyclohexyl and 3-phenylpropyl radicals to (Z)-2 derived from aldehyde 3 gave β-addition products with syn-stereoselectivity (syn:anti = 8.6:1 - syn only).The reactions of (E)-2 were non-stereoselective.Based on allylic strain, a transition-state model for the syn-stereoselectivity is proposed. 1,2-Asymmetric induction was carried out in radical cyclisation to synthesize optically active cyclohexane derivatives.
Diastereoselectivity of the conjugate addition of organocopper reagents to γ-alkoxy α,β-unsaturated carbonyl derivatives. Importance of the reagent type and the double-bond geometry
Yamamoto, Yoshinori,Chounan, Yukiyasu,Nishii, Shinji,Ibuka, Toshiro,Kitahara, Haruo
, p. 7652 - 7660 (2007/10/02)
Systematic investigations of the diastereoselectivity of organocopper conjugate addition to γ-alkoxy trans enoates (3), cis enoates (4), and diesters (5) revealed that the selectivity highly depended on the substrate structure and the reagent type. The an
