- Regio-selective synthesis of 1,2-aminoalcohols from epoxides and chlorohydrins
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A simple and efficient procedure for the regio-selective synthesis of 1,2-aminoalcohols from terminal epoxides and chlorohydrins by using NaHMDS as the source of amine is reported. The wider scope and utility of this method is demonstrated.
- Murugan, Andiappan,Kadambar, Vasantha Krishna,Bachu, Sreekanth,Rajashekher Reddy,Torlikonda, Venkatarao,Manjunatha, Sulur G.,Ramasubramanian, Sridharan,Nambiar, Sudhir,Howell, Gareth P.,Withnall, Jane
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- Asymmetric synthesis of ephedrine analogs
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Addition of nitromethane to the chiral chromium tricarbonyl complex of o-tolualdehyde (1) gives, under conditions of kinetic control, the nitroalcohol 2 with ca. 95percent of asymmetric induction.Compound 2 then gives, in 3 steps, the corresponding aminoalcohol in about 40percent.Use of nitroethane gives the nitroalcohol with a small diastereoselectivity at C(2)-C(3) (d.e. = 30 and 55percent), but analogs of ephedrine and pseudoephedrine can be obtained optically pure by chromatography.
- Solladie-Cavallo, A.,Lapitajs, G.,Buchert, P.,Klein, A.,Colonna, S.,Manfredi, A.
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- Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
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A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.
- Yang, Hui,Zheng, Wen-Hua
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supporting information
p. 16177 - 16180
(2019/11/03)
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- Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines
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The 1,3-diamine motif appears in numerous complex molecules, yet there are few methods for the stereoselective construction of this moiety. Herein, we demonstrate a stereocontrolled synthesis of 1,3-diamines, which bear up to three contiguous stereogenic centers, through benzylic ring-opening of aziridines with 2-azaallyl anion nucleophiles. Reactions proceed efficiently (yield up to 95%), diastereoselectively (dr up to >20:1), site selectively, and enantiospecifically to deliver products with differentiated amino groups.
- Li, Kangnan,Weber, Alexandria E.,Tseng, Luke,Malcolmson, Steven J.
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supporting information
p. 4239 - 4242
(2017/08/23)
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- Direct catalytic synthesis of unprotected 2-amino-1-phenylethanols from alkenes by using iron(II) phthalocyanine
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Aryl-substituted amino alcohols are privileged scaffolds in medicinal chemistry and natural products. Herein, we report that an exceptionally simple and inexpensive FeII complex efficiently catalyzes the direct transformation of simple alkenes into unprotected amino alcohols in good yield and perfect regioselectivity. This new catalytic method was applied in the expedient synthesis of bioactive molecules and could be extended to aminoetherification.
- Legnani, Luca,Morandi, Bill
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supporting information
p. 2248 - 2251
(2016/02/18)
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- PYRIMDINE COMPOUNDS USEFUL AS KINASE INHIBITORS
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A compound of formula (I) or a salt or solvate thereof: Formula (1) compositions and medicaments containing the same, as well as processes for the preparation and use of such compounds, compositions and medicaments. Such mono-anilino pyrimidine derivative
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Page/Page column 37-38
(2010/11/30)
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- ARENE-CHROMIUM-TRICARBONYL COMPLEXES: STEREOSELECTIVE REACTIONS WITH ISOCYANIDE
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More than 98 percent of A.I. is obtained during addition of TosMic with chiral complexes 2 and 3.The diastereoselectivity of the formation of the oxazolines is studied and the diastereomers clearly assigned.Orbital-interactions and electronic repulsions s
- Solladie-Cavallo, A.,Quazzotti, S.,Colonna, S.,Manfredi, A.
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p. 2933 - 2936
(2007/10/02)
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- Highly Diastereoselective Synthesis of Aminoalcohols of Ephedrine Type
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Analogs of ephedrine are obtained in 80percent yield in 3 steps from chiral arenechromium tricarbonyl complexes.Hence optically pure complexes afford optically pure analogs of ephedrine.
- Solladie-Cavallo, Arlette,Dreyfus, Anne-Claire,Sanch, Francois,Klein, Arlette
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p. 1583 - 1586
(2007/10/02)
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