58463-02-8Relevant articles and documents
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Lutz,R.P. et al.
, p. 2048 - 2049 (1976)
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An unprecedented stereoselective titanium-mediated dihydrodimerization of allyl ethers and allylamines
De Meijere, Armin,Stecker, Bj?rn,Kourdioukov, Alexandre,Williams, Craig M.
, p. 929 - 934 (2000)
3-Phenylallyl ether 17, 2,5-dihydrofuran (1) and N-acceptor-substituted 2,5-dihydropyrrols 4, 6, 8, 10, 12 upon treatment with cyclohexylmagnesium bromide in the presence of Ti(Oi-Pr)4 were found to undergo a diastereoselective dihydrodimerization affording 1,5-dienes, d,1-2,3- diethenylbutane-1,4-diol (51% yield) and d,1-2,3-diethenyl-1,4- bis(sulfonylamino)butanes (43-52%), respectively. In the presence of titanium bis(4R,5R)-taddolate, the dihydrodimerization of 1 proceeded with 35-38% chemical yield and up to 94% ee.
Cobalt-Catalyzed Diastereo- And Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates
Wang, Lei,Wang, Lifan,Li, Mingxia,Chong, Qinglei,Meng, Fanke
, p. 12755 - 12765 (2021/08/30)
Catalytic generation of ambiphilic π-allyl-metal complexes and their utility in enantioselective transformations constitutes a powerful approach for introduction of allyl groups to a molecule. Herein an unprecedented cobalt-catalyzed highly site-, diastereo-, and enantioselective protocol for stereoselective formation of nucleophilic allyl-Co(II) complexes followed by addition to aldehydes is presented. The reaction features diastereo- and enantioconvergent conversion of easily accessible allylic alcohol derivatives to diversified enantioenriched homoallylic alcohols with a remarkably broad scope of allyl groups that can be introduced. Mechanistic studies indicated that allyl radical intermediates were involved in this process. These new discoveries establish a new strategy for development of enantioselective transformations through capture of radicals by chiral Co complexes, pushing forward the frontier of Co complexes for enantioselective catalysis.
Nickel-Catalyzed Homo- And Cross-Coupling of Allyl Alcohols via Allyl Boronates
Gan, Yi,Hu, Hui,Liu, Yuanhong
supporting information, p. 4418 - 4423 (2020/06/27)
A nickel-catalyzed homo- and cross-coupling of allylic alcohols to 1,5-dienes in the presence of B2pin2 with excellent regioselectivity has been developed. Mechanistic studies indicate that the reaction proceeds via sequential nickel-catalyzed borylation of allyl alcohols followed by cross-coupling of the resulting allyl boronates with allyl alcohols. The method was effectively applied to nickel-catalyzed allylation of aldehydes using allylic alcohols directly.
Copper-catalysed α-selective allylic alkylation of heteroaryllithium reagents
Vila, Carlos,Hornillos, Valentn,Faans-Mastral, Martn,Feringa, Ben L.
, p. 9321 - 9323 (2014/12/11)
2-Allyl-substituted thiophenes and furans are synthesised efficiently in a direct procedure using 2-heteroaryllithium reagents and allyl bromides and chlorides catalysed by ligand-free copper(i). The reactions take place under mild conditions, with excellent α-selectivity, high functional group tolerance and good yields for the SN2 products. This journal is
