94607-75-7Relevant academic research and scientific papers
Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals
Ito, Suguru,Hayashi, Akira,Komai, Hirotomo,Yamaguchi, Hitoshi,Kubota, Yoshihiro,Asami, Masatoshi
, p. 2081 - 2089 (2011/04/19)
A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both carbonyl compounds and acetals with allylsilanes to afford the corresponding homoallyl silyl ethers and homoallyl alkyl ethers, respectively. Both the mesoporous structure and the presence of aluminum moiety were indispensable for the high catalytic activity of Al-MCM-41. Moreover, Al-MCM-41 could catalyze the reaction of acetals chemoselectively in the presence of the corresponding carbonyl compounds. The solid acid catalyst Al-MCM-41 could be recovered easily by filtration and could be reused three times without a significant loss of catalytic activity.
Zinc mediated allylation of aldehydes and ketones using allyl bromides and commercial zinc dust. the issue of regio- And stereoselectivity
Majee, Adinath,Das, Asish R.,Ranu, Brindaban C.
, p. 731 - 736 (2007/10/03)
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. Excellent regioselectivity has been observed in the reaction of substituted allyl bromides.
Ligand effects in selective addition reactions of organoindium reagents with carbonyl compounds
Reetz, Manfred T.,Haning, Helmut
, p. 117 - 120 (2007/10/03)
The reaction of the allyl indium sesquibromide (CH2 =CHCH2)3In2Br3 with four equivalents of a bulky lithium alkoxide ((CH3)3COLi or (CH3)3CCH2OLi) results in modified reagents which show unusual degrees of chemo-and stereoselectivity in reactions with carbonyl compounds. For example, in reactions with cyclohexanone derivatives, 84-93% equatorial attack with preferential formation of the axial alcohols is observed. Chiral aldehydes react in a highly diastereoselective manner.
Stereoselective Addition of Organotitanium Reagents to Carbonyl Compounds
Reetz, Manfred T.,Steinbach, Rainer,Westermann, Juergen,Peter, Roland,Wenderoth, Bernd
, p. 1441 - 1454 (2007/10/02)
Titanation of alkyllithium or -magnesium compounds using ClTi(OR)3 results in reagents which show markedly increased diastereofacial selectivity (80 - 90percent) in reactions with α-chiral aldehydes or ketones.Titanation is also the method of choice in Grignard-type additions to substituted cyclohexanones; CH3Ti(OCHMe2)3 (6a) adds predominantly from the equatorial direction, while allyltitanium reagents 11b and 12 show axial preference.Crotyltitanium compounds react with carbonyl compounds to afford primarily adducts having anti-configuration, a process which is of particular value in case of ketones (anti/syn ratios up to 99:1).Titanation of (trimethylsilyl)allyllithium (48) with Ti(OCHMe2)4 reverses regioselectivity in reactions with aldehydes and ketones, β-hydroxy silanes 50 being the only observed products.These have anti-configuration and can be converted either into Z- or E-dienes using the Peterson elimination under basic or acidic conditions, respectively.
