1123-34-8Relevant academic research and scientific papers
Dibutyltin oxide mediated diastereoselective cyclodehydration/sulfonylation of 1,2,4-triols
Gamedze, Makhosazana P.,Nkambule, Comfort M.
, p. 1825 - 1829 (2015)
Dibutyltin oxide (Bu2SnO) mediated cyclodehydration or sulfonylation of 1,2,4-triols is predictably diastereoselective depending on the steric bulk of the substituents at C4. A larger difference (ΔA-value >1 kcal/mol) leads to the syn-1,2,4-triols favouring cyclodehydration (78-85%) to form 3-hydroxytetrahydrofurans, with the anti-1,2,4-triols favouring monosulfonylation (66-87%). Triols from symmetrical ketones preferentially undergo cyclodehydration in high yield (>75%) due to a gem-disubstituent effect. Thus, the 1,2,4-triols derived from simple cyclic ketones also favour cyclodehydration to form spirocyclic 3-hydroxytetrahydrofurans in 72-79% yields.
Allylic Phosphates as Allyl Anion Synthons. Lithium-induced Allylation of Carbonyl Compounds
Araki, Shuki,Butsugan, Yasuo
, p. 457 - 458 (1988)
Ultrasonication of allylic phosphates and carbonyl compounds with a lithium powder gave high yields of the corresponding homoallylic alcohols.
Scandium trifluoromethanesulfonate-catalyzed chemoselective allylation reactions of carbonyl compounds with tetraallylgermane in aqueous media
Akiyama, Takahiko,Iwai, Junko,Sugano, Megumi
, p. 7499 - 7508 (1999)
Scandium(III) triflate-catalyzed allylation of carbonyl compounds with tetraallylgermane proceeded readily in aqueous nitromethane to afford homoallyl alcohols in excellent to good yields. The presence of H2O is indispensable for the allylation
GRIGNARD-TYPE ALLYLATION OF CARBONYL COMPOUNDS IN METHANOL BY THE ELECTROCHEMICALLY RECYCLED ALLYLTIN REAGENT.
Uneyama, Kenji,Matsuda, Hiroyuki,Torii, Sigeru
, p. 6017 - 6020 (1984)
An electrochemical allylation of aldehydes and ketones in methanol was achieved by the electroreductive regeneration of diallyltin reagent in the presence of a catalytic amount of tin, affording the corresponding homoallyl alcohols in 72 - 91percent yield
Facile and Efficient Synthesis of Homoallylic Alcohols Using Allyl Bromide and Commercial Zinc Dust
Ranu, Brindaban C.,Majee, Adinath,Das, Asish R.
, p. 4885 - 4888 (1995)
An efficient procedure for the preparation of homoallylic alcohols has been achieved by a simple reaction of an aldehyde or a ketone with allyl bromide and commercial zinc dust in tetrahydrofuran.
Protic solvent-promoted neutral allylation of aldehydes and ketones with 1,8-bis(allylstannyl)naphthalenes
Asao, Naoki,Abe, Noriko,Tan, Zheng,Maruoka, Keiji
, p. 377 - 378 (1998)
The allylation reactions of carbonyl compounds using 1,8-bis(dibutylstannyl)naphthalene 1 (R = Bu) were dramatically promoted by using a mixture of THF and CF3CH2OH (5 : 1) as solvent. The rate acceleration was due to the enhancement
Indium-mediated allylation of carbonyl compounds in deep eutectic solvents
González-Gallardo, Nerea,Saavedra, Beatriz,Guillena, Gabriela,Ramón, Diego J.
, (2021)
This study describes, for the first time, the in situ generation of indium organometallic reagents in environmentally friendly deep eutectic solvents (DESs). The allylation process of different carbonyl compounds is achieved mediated by indium metal and u
Synthesis of homoallylic alcohols from ketones in water
Wang, Jun,Yuan, Gu
, p. 401 - 405 (2006)
Homoallylic alcohols have been prepared in good yields by allylation of ketones with allyl bromide in the presence of stannous chloride dihydrate, zinc iodide, and ammonium chloride in water. Copyright Taylor & Francis LLC.
Solvent-Mediated Allylation of Carbonyl Compounds with Allylic Stannanes
Cokley, Teresa M.,Harvey, Peta J.,Marshall, Raymond L.,McCluskey, Adam,Young, David J.
, p. 1961 - 1964 (1997)
Methanol promotes the addition of allyltrimethylstannane (1a) to isobutyraldehyde (2a, 30 °C) yielding the corresponding homoallylic alcohol (3a), without the necessity for added catalyst. The corresponding reaction of aldehydes 2a-e or activated ketone 2
Organometallic reactions in aqueous media: The allylations of carbonyl compounds mediated in Zn/CdSO4 and Zn/SnCl2 bimetal systems
Zhou, Cunliu,Zhou, Yuqing,Jiang, Jiaoyang,Xie, Zhen,Wang, Zhiyong,Zhang, Jiahai,Wu, Jihui,Yin, Hao
, p. 5537 - 5540 (2004)
Zn/CdSO4 and Zn/SnCl2 bimetal systems were employed in the allylations of aldehydes or ketones in distilled water to afford the corresponding homoallylic alcohols in good yields. Also, the chemoselectivity was studied under the same
