22787-68-4Relevant academic research and scientific papers
Modular and Stereoselective Approach to Highly Substituted Indole/Pyrrole-Fused Diazepanones
Wang, Shutao,Wang, Siyu,Song, Shaoli,Gao, Qiansong,Wen, Chunxi,Zhang, Zhuoqi,Zheng, Lianyou,Xiang, Jinbao
, p. 6458 - 6466 (2021/05/29)
A one-pot synthetic method for indole/pyrrole-fused 1,4-diazepanone scaffolds has been developed. This method involves a sequential amide coupling/intramolecular aza-Michael addition of 1H-indole/pyrrole-2-carboxylic acids with Morita-Baylis-Hillman-deriv
The alkoxycarbonylation of protected propargyl alcohols
Alam, Md. Mahbubul,Beghetto, V.,Bertoldini, M.,Scrivanti, A.,Sole, R.
, (2020/09/02)
Palladium-catalyzed alkoxycarbonylation of the C≡C triple bond of propargyl alcohol is a sustainable synthetic approach to 2-(hydroxymethyl)acrylates, a family of valuable intermediates. The developed synthetic protocol includes protection of the alcoholic function of the alkyne before its carbonylation in the presence of Drent's catalytic system. Protection step effectively extends the catalyst life hence enhancing the practical applicability of the reaction. The effectiveness of some different protecting groups (benzyl, acetyl and trimethylsilyl) has been assessed and the influence of the reaction parameters investigated.
A general approach to the synthesis of β2-amino acid derivatives via highly efficient catalytic asymmetric hydrogenation of α-aminomethylacrylates
Guo, Yujuan,Shao, Guang,Li, Lanning,Wu, Wenhao,Li, Ruihong,Li, Jingjing,Song, Jian,Qiu, Liqin,Prashad, Mahavir,Kwong, Fuk Yee
experimental part, p. 1539 - 1553 (2010/08/22)
A new strategy was developed for the synthesis of a valuable class of α-aminomethylacrylates via the Baylis-Hillman reaction of different aldehydes with methyl acrylate followed by acetylation of the resulting allylic alcohols and SN2′-type amination of the allylic acetates. Asymmetric hydrogenation of these diverse olefinic precursors using rhodium(Et-Duphos) catalysts provided the corresponding β2-amino acid derivatives with excellent enantioselectivities and exceedingly high reactivities (up to >99.5% ee and S/C=10,000). The first hydrogenation of (Z)-configurated substrates was studied for the synthesis of β2-amino acid derivatives. The high influence of the substrate geometry and steric hindrance on the reactivity and enantioselectivity was also disclosed for this reaction. This protocol provides a highly practical, facile and scalable method for the preparation of optically pure β2- amino acids and their derivatives under mild reaction conditions.
Synthesis of α-alkylidene-δ-valerolactones via the conjugate addition of ketone enolates to functionalized allyl acetates
Ramachandran, P. Veeraraghavan,Bhattacharyya, Annyt
scheme or table, p. 863 - 872 (2010/10/01)
Sequential addition of ketone enolates to allyl acetates bearing an ester, followed by reduction and cyclization provides a variety of substituted α-alkylidene-δ-valerolactones.
Total synthesis of the eupomatilones
Mitra, Soumya,Gurrala, Srinivas Reddy,Coleman, Robert S.
, p. 8724 - 8736 (2008/03/12)
(Chemical Equation Presented) Full details of the total syntheses of five members of the eupomatilone family of lignans are reported.
Novel Functionalized Trisubstituted Allylboronates via Hosomi-Miyaura Borylation of Functionalized Allyl Acetates
Ramachandran, P. Veeraraghavan,Pratihar, Debarshi,Biswas, Debanjan,Srivastava, Amit,Reddy, M. Venkat Ram
, p. 481 - 484 (2007/10/03)
(Equation presented) A series of novel functionalized achiral and chiral allylboronates have been synthesized via the nucleophilic addition of boronates on allyl acetates derived via vinylalumination or Baylis-Hillman reaction of aldehydes. These reagents
One-pot facile conversion of Baylis-Hillman adduct into N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione. Formal synthesis of tacamonine
Chen, Chung-Yi,Chang, Meng-Yang,Hsu, Ru-Ting,Chen, Shui-Tein,Chang, Nein-Chen
, p. 8627 - 8630 (2007/10/03)
A stepwise [3+3] strategy to N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione 1 used various N-alkyl α-substituted sulfonylacetamides 2 and α,β-unsaturated esters 3 as starting materials. α,β-Unsaturated esters 3 were generated by Baylis-Hillman reaction. A ring closure mechanism was proposed for the reactions. This method provides a convenient formal synthesis of tacamonine.
1,3-Dipolar Cycloadditions to Baylis-Hillman Adducts: Rationale for the Observed Diastereoselectivity
Annunziata, Rita,Benaglia, Maurizio,Cinquini, Mauro,Cozzi, Franco,Raimondi, Laura
, p. 4697 - 4706 (2007/10/02)
Diazomethane and benzonitrile oxide cycloadditions were performed on Baylis-Hillman adducts derived from methyl acrylate and aldehydes (β'-alkoxy-α,β-unsaturated esters).The reactions proceed in good chemical yields, and their stereochemical outcome can b
Enzymatic process for preparing optically active 3-substituted azetidinones
-
, (2008/06/13)
Preparation of optically active 3-substituted azetidinones of the formula (I) STR1 in which R1 is a hydroxy-protective group wherein an allylic alcohol of the formula (II) STR2 is acylated, then subjected to asymmetric enzymatic hydrolysis yiel
Necic Acid Synthons. Part 5. Total Synthesis of (+/-)-Retronecic Acid and Related Compounds via Zinc-Mediated Coupling of Halogeno-esters
Ameer, Farouk,Drewes, Siegfried E.,Hoole, Robyn,Kaye, Perry T.,Pitchford, Andrew T.
, p. 2713 - 2718 (2007/10/02)
Zinc-mediated coupling of suitably substituted halogeno esters affords access to (+/-)-retronecic acid (2) and related intermediates.These approaches lead to racemic retronecic acid on the one hand and to a diastereoisomeric mixture of the acid on the other.
