- Highly diastereoselective tandem reduction-allylation reactions of 1,4-diketones with zirconocene-olefin complexes
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Terminal alkenes act as dual nucleophiles in a zirconocene-mediated, highly 1,4-diastereoselective, tandem reduction-allylation reaction of 1,4-diketones. A zirconocene-alkene complex (in equilibrium with an allyl-zirconocene-hydride species) can deliver both hydride and an allyl group to a diketone, with control of the relative configuration of up three new stereogenic centers (see scheme).
- Fujita, Kazuya,Shinokubo, Hiroshi,Oshima, Koichiro
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Read Online
- Nickel-catalyzed reductive allylation of ketones with allylic carbonates
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Nickel-catalyzed efficient umpolung allylation of ketones with allylic carbonates in the presence of zinc powder is developed, which accommodates a variety of allylic and ketone substrates. Although chiral ligand is necessary for the transformation, no enantioselectivity was observed. Georg Thieme Verlag Stuttgart New York.
- Zhao, Chenglong,Tan, Zhuozhen,Liang, Zhuye,Deng, Wei,Gong, Hegui
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supporting information
p. 1901 - 1907
(2014/07/22)
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- Catalytic use of a soluble organoindium(III) species for allylation and crotylation of ketones with boronates
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The unprecedented use of a soluble organoindium species, indium(III) hexamethyldisilazide [In(III)(hmds)3], for catalytic carbon-carbon bond formations between ketones and boronates, is reported. Various functionalized tertiary homoallyl alcoho
- Yamaguchi, Miyuki,Morita, Naohide,Schneider, Uwe,Kobayashi, Shu
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experimental part
p. 1461 - 1465
(2010/08/20)
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- Catalytic use of indium(0) for carbon-carbon bond transformations in water: General catalytic allylations of ketones with allylboronates
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We have discovered the unprecedented catalytic use of In(0) for catalytic C-C bond transformations. Remarkably, these general catalytic allylations of ketones proceeded smoothly in water as a sole solvent under mild conditions, and water proved to be essential for these reactions. Both the displayed substrate scope and the functional group tolerance were excellent. Importantly, the In metal catalyst could be easily recovered and reused without loss of catalytic activity. Moreover, when an α-substituted allylboronate was used, an unusual constitutional selectivity was observed providing exclusively the formal α-adduct. Additionally, the resulting tertiary homoallylic alcohols were obtained with exceptionally high diastereoselectivities. The applicability of this concept to asymmetric catalysis in water by using In(0) combined with a chiral bis(oxazoline) ligand was demonstrated as well. Copyright
- Schneider, Uwe,Ueno, Masaharu,Kobayashi, Shu
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supporting information; experimental part
p. 13824 - 13825
(2009/02/07)
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- An efficient method for allylation of ketones with tetra-allylstannane
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A variety of ketones undergo an allylation reaction with tetra-allyltin in the presence of a catalytic amount of Cu(OTf)2 or Sn(OTf)2. The method was found to be superior to most of the known methods, which are efficient only with al
- Kamble, Rajesh M,Singh, Vinod K
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p. 7525 - 7526
(2007/10/03)
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- Zinc mediated allylation of aldehydes and ketones using allyl bromides and commercial zinc dust. the issue of regio- And stereoselectivity
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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.
- Majee, Adinath,Das, Asish R.,Ranu, Brindaban C.
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p. 731 - 736
(2007/10/03)
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- Facile and Efficient Synthesis of Homoallylic Alcohols Using Allyl Bromide and Commercial Zinc Dust
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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.
- Ranu, Brindaban C.,Majee, Adinath,Das, Asish R.
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p. 4885 - 4888
(2007/10/02)
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- Organomanganese (II) reagents XX1: Manganese mediated Barbier and Reformatsky like reactions. An efficient route to homoallylic alcohols and β-acetoxyesters
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Allylic halides and α-bromoesters react with manganese metal in ethyl acetate; THF can also be used as solvent if a catalytic amount of zinc chloride is added to the reaction mixture. When the reaction is performed in the presence of various aldehydes or
- Cahiez,Chavant
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p. 7373 - 7376
(2007/10/02)
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