61390-40-7Relevant articles and documents
Practical acetalization and transacetalization of carbonyl compounds catalyzed by recyclable PVP-I
Cao, Fu-Rong,Lu, Guangying,Ren, Jiangmeng,Wang, Di,Zeng, Bu-Bing
, (2021/06/21)
A novel PVP-I catalyzed acetalizations/transacetalizations of carbonyl compounds has been developed processing with a mild and easy handling fashion. Different types of Acyclic and cyclic acetals were prepared from carbonyl compounds or their acetals successfully. Further applications of newly developed catalytic combination were testified. This protocol featured with simplicity of operation, mild reaction condition, short reaction time, recyclable of catalyst and broad substrates scope with excellent yields.
Zinc borates: Functionalized hard nucleophiles for coupling reactions with secondary allylic acetates
Kobayashi, Yuichi,Tokoro, Yuko,Watatani, Kengo
, p. 3825 - 3834 (2007/10/03)
We have succeeded in developing zinc borates of the general structure 3 for coupling reaction with allylic acetates. The advantages of using compounds 3 are their compatibility with carbonyl groups such as aldehyde, ketone, and ester groups, and their high reactivity toward secondary allylic acetates. Zinc borates 3 were prepared from boronate esters 1 [R(T) = p-(CHO)C6H4, p-(Ac)C6H4, p-{Ac(CH2)2}C6H4, p-(Ac-OCH2)C6H4, p-{AcO(CH2)3}C6H4, p-{EtO2C(CH2}2}C6H4, (E)-CH=CH(CH2)4OAc] with MeZnCl; subsequent treatment with allylic acetates 4 [R = n-C5H11, c-C6H11, (CH2)2CH(-O(CH2}2O-)] in the presence of NiCl2(PPh3)2 (10 mol-%) in THF-DMI (1,3-dimethyl-2-imidazolidinone) (10 equiv.) at 40-50 °C overnight furnished the coupling products 5 in good yields. Among the products, 5bb, possessing one free and one protected aldehyde group, is a highlight of this type of reaction. The stereochemical aspects of the reaction were also examined. Thus, the alkenyl groups of (E)- and (Z)-alkenyl borates 3b and c were transformed with retention of the olefinic geometry into acetates 4a and b (R = n-C5H11, c-C6H11), while reaction of cyclic acetate 11 proceeded with inversion at the carbon center involved in the reaction. In addition, we found that the anions generated from (EtO)2P(= O)CH2CO2Et and (MeO)2P(=O)CH2Ac under Masamune's conditions attacked the aldehyde carbon in the boronate 1d to produce - after reduction of the double bond - the boronate esters 1i and 1j, respectively, in good yields.