139313-43-2Relevant academic research and scientific papers
Allylsamarium bromide-mediated cascade cyclization of homoallylic esters. Synthesis of 2-(2-hydroxyalkyl)cyclopropanols and 2-(2-hydroxyethyl)bicyclo[2.1.1]hexan-1-ols
Shen, Mengmeng,Tu, Yawei,Xie, Guanqun,Niu, Qingsheng,Mao, Hui,Xie, Tingting,Flowers, Robert A.,Lv, Xin,Wang, Xiaoxia
, p. 52 - 61 (2016/09/12)
In continuation of our previous study on the intramolecular reductive coupling of simple homoallylic esters promoted by allylSmBr/HMPA/H2O, which afforded a facile synthesis of 2-(2-hydroxyalkyl)cyclopropanols, here we report the reductive casc
Study on the coupling of acyclic esters with alkenes - The synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide
Tu, Yawei,Zhou, Liejin,Yin, Ruifeng,Lv, Xin,Flowers Ii, Robert A.,Choquette, Kimberly A.,Liu, Huili,Niu, Qingsheng,Wang, Xiaoxia
supporting information, p. 11026 - 11028 (2013/01/15)
The radical cyclization between aliphatic acyclic esters and alkenes was achieved unprecedentedly in the presence of allylsamarium bromide with HMPA and H2O as additives. The cascade radical cyclization-ring-opening- anionic cyclization allowed facile and efficient access to 2-(2-hydroxyalkyl) cyclopropanols from readily available materials.
Formation of chiral tertiary homoallylic alcohols via Evans aldol reaction or enzymatic resolution and their influence on the Sharpless asymmetric dihydroxylation
Theurer, Matthias,Fischer, Peter,Baro, Angelika,Nguyen, Giang Son,Kourist, Robert,Bornscheuer, Uwe,Laschat, Sabine
experimental part, p. 3814 - 3823 (2010/07/04)
Enantioenriched tertiary homoallylic alcohol derivatives (S)-2c and (S)-2a were obtained via Evans aldol methodology and enzymatic resolution of racemic tertiary acetate 2e, respectively. In order to study asymmetric 1,3-induction of the stereogenic cente
Substituent effects on cyclobutyl and cyclopropylcarbinyl cations
Wiberg, Kenneth B.,Shobe, David,Nelson, Gordon L.
, p. 10645 - 10652 (2007/10/02)
The acetolyses of 3-substituted cyclobutyl tosylates (X = Ar, Cl, and OEt) were examined giving rate constants and product distributions. With the alkyl- and aryl-substituted compounds, the rate-determining step leads to the formation of a bridged cyclobu
Cobalt(II) Chloride Catalyzed Acylation of Alcohols with Acetic Anhydride: Scope and Mechanism
Iqbal, Javed,Srivastava, Rajiv Ranjan
, p. 2001 - 2007 (2007/10/02)
Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield.Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones.Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate.The β-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting β-acetoxy carbonyl compound is observed.A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene.A mechanism for these acylations is proposed by invoking an electron-transfer process.
