- Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols
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Chiral biphenols catalyze the asymmetric Petasis borono-Mannich allylation of aldehydes and amines through the use of a bench-stable allyldioxaborolane. The reaction proceeds via a two-step, one-pot process and requires 2–8 mole % of 3,3′-Ph2-BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti- and syn-diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E- and Z-borolane stereoisomers.
- Jiang, Yao,Schaus, Scott E.
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p. 1544 - 1548
(2017/02/05)
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- An efficient three-component synthesis of homoallylic amines catalysed by MgI2 etherate
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A three-component reaction of aldehydes, amines and allyltributylstannane was efficiently carried out to afford the corresponding homoallylic amine derivatives in the presence of 20 mol% of MgI2 etherate [(MgI 2?(OEt2)n] under mild and neutral reaction conditions in good to excellent yields.
- Wang, Yanping,Liu, Yingshuai,Hu, Shenghui,Zhang, Xingxian
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experimental part
p. 21 - 24
(2012/03/27)
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- Palladium-catalyzed, one-pot, three-component synthesis of homoallylic amines from aldehydes, anisidine, and allyl trifluoroacetate
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(Chemical Equation Presented) An allylation reaction that generates homoallylic amines using allyl trifluoroacetate as a nucleophilic allylmetal precursor is reported. A palladium complex catalyzes two transformations in one pot: formation of allylsilane
- Grote, Robin E.,Jarvo, Elizabeth R.
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supporting information; experimental part
p. 485 - 488
(2009/07/18)
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- Three components synthesis of homoallylic amines catalyzed by bismuth(III) nitrate pentahydrate
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Bismuth (III) nitrate pentahydrate catalyzes efficiently the three-component condensation of aldehydes, amines, and allyltributylstannane at rt to afford the corresponding homoallylic amines in excellent yield.
- Thirupathi, Ponnaboina,Kim, Sung Soo
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experimental part
p. 5168 - 5173
(2009/12/01)
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- Palladium-catalyzed allylation of imines with allyl alcohols
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(Chemical Equation Presented) A catalytic system, Pd(OAc)2 (10 mol %)-P(n-Bu)3 (20 mol %)-Et3B (360 mol %), promotes allylic alcohols to undergo the allylation of anisidineimines of aromatic and aliphatic aldehydes and furnishes homoallylamines in good to moderate yields. The reaction shows unique stereoselectivity, giving anti-isomers selectively.
- Shimizu, Masamichi,Kimura, Masanari,Watanabe, Toshiya,Tamaru, Yoshinao
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p. 637 - 640
(2007/10/03)
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- New synthetic approach to substituted isoindolo[2,1-a]quinoline carboxylic acids via intramolecular Diels-Alder reaction of 4-(N-furyl-2)-4- arylaminobutenes-1 with maleic anhydride
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Acylation of substituted 4-(furyl-2)-4-arylaminobut-1-enes with maleic anhydride provided 2-allyl-6-carboxy-4-oxo-3-aza-10-oxatricyclo[5.2.1.0 1,5]dec-8-enes in high yield under mild reaction conditions. The Diels-Alder adducts are formed via an initial amide formation followed by a stereoselective intramolecular [4+2] exo-cycloaddition reaction. Treatment of the tricyclic compounds with phosphoric acid at high temperatures (70-120°C) promoted cyclic ether opening, intramolecular cyclization and aromatization to give the corresponding tetracyclic compounds, 5,6,6a,11-tetrahydro-10- carboxyisoindolo[2,1-a]quinolines, in moderate yields. The influence of the acid and the reaction temperature on the cyclization reactions are also discussed.
- Zubkov, Fedor I.,Boltukhina, Ekaterina V.,Turchin, Konstantin F.,Borisov, Roman S.,Varlamov, Alexey V.
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p. 4099 - 4113
(2007/10/03)
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- Synthesis of polystyrene-bound perfluoroalkyl sulfonic acids and the application of their ytterbium salts in multicomponent reactions (MCRs)
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New polystyrene-bound perfluoroalkyl sulfonic acids and their ytterbium salts have been prepared. Multicomponent reactions (MCRs) for the efficient synthesis of homoallylic amines or amides catalyzed by the polystyrene-bound perfluoroalkyl sulfonic ytterb
- Yin, Yueyan,Zhao, Gang,Li, Gui-Long
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p. 12042 - 12052
(2007/10/03)
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- Allylation of imines with allyltrimethylsilane and experimental evidences for a fluoride-triggered autocatalysis mechanism of the Sakurai- Hosomi reaction
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This article reports the reaction of allyltrimethylsilane 1 with aldimines 2 in the presence of tetra-n-butylammonium fluoride to give the corresponding homoallylamines 3 in moderate to excellent yields. The allylation mechanism of imines as well as that of aldehydes can be reasonably interpreted by a fluoride-triggered autocatalytic procedure.
- Wang, De-Kun,Zhou, Yong-Gui,Tang, Yong,Hou, Xue-Long,Dai, Li-Xin
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p. 4233 - 4237
(2007/10/03)
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- Allylstannane Allylation of Aldimines Activated by Chlorotrimethylsilane
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Aldimines activated by chlorotrimethylsilane reacted with allylstannane to give the corresponding homoallylic amines with excellent yields.
- Wang, De-Kun,Dai, Li-Xin,Hou, Xue-Long
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p. 8649 - 8652
(2007/10/02)
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