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Synthetic Communications

An International Journal for Rapid Communication of Synthetic Organic Chemistry

Volume 27, 1997 - Issue 20

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Original Articles

Practical Oxirane Ring Opening with In Situ Prepared LiCN; Synthesis of (2S,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)-1-butanenitrile

Akihiko Tsuruoka Toshihiko Naito, Norio Minami. Eisai Co. Ltd., Tsukuba Research Laboratories, 1—3 Tokodai 5 chome Tsukuba, Ibaraki, Japan, 300—26

Shigeto Negi Toshihiko Naito, Norio Minami. Eisai Co. Ltd., Tsukuba Research Laboratories, 1—3 Tokodai 5 chome Tsukuba, Ibaraki, Japan, 300—26

Manabu Yanagisawa Toshihiko Naito, Norio Minami. Eisai Co. Ltd., Tsukuba Research Laboratories, 1—3 Tokodai 5 chome Tsukuba, Ibaraki, Japan, 300—26

Kazumasa Nara Toshihiko Naito, Norio Minami. Eisai Co. Ltd., Tsukuba Research Laboratories, 1—3 Tokodai 5 chome Tsukuba, Ibaraki, Japan, 300—26

Pages 3547-3557 | Received 18 Feb 1997, Published online: 22 Aug 2006

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https://doi.org/10.1080/00397919708007076

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Ankita Chakraborty, Avula Shiva Krishna, Gurrala Sheelu, Subhash Ghosh & Thenkrishnan Kumaraguru. (2022) pH-controlled regioselective nucleophilic ring-opening of epoxide: an improved process for the preparation of ( R )-(−)- or ( S )-(+)-3-hydroxytetrahydrofuran . Organic & Biomolecular Chemistry 20:34, pages 6863-6868.
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Elham Ghobadi, Shahnaz Saednia & Saeed Emami. (2022) Synthetic approaches and structural diversity of triazolylbutanols derived from voriconazole in the antifungal drug development. European Journal of Medicinal Chemistry 231, pages 114161.
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M. Shaheer Malik, Basim H. Asghar, Shaik Azeeza, Rami J. Obaid, Ismail I. Thagafi, Rabab.S. Jassas, Hatem M. Altass, Moataz Morad, Ziad Moussa & Saleh A. Ahmed. (2020) Facile Amberlyst A-21 catalyzed access of β-hydroxynitriles via epoxide opening in water. Arabian Journal of Chemistry 13:11, pages 8200-8208.
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Mehdi Fallah-Mehrjardi, Ali Reza Kiasat & Khodabakhsh Niknam. (2018) Nucleophilic ring-opening of epoxides: trends in β-substituted alcohols synthesis. Journal of the Iranian Chemical Society 15:9, pages 2033-2081.
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Hossein Naeimi & Azam Karshenas. (2013) Highly regioselective conversion of epoxides to β-hydroxy nitriles using metal(II) Schiff base complexes as new catalysts under mild conditions. Polyhedron 49:1, pages 234-238.
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Gabriele Bianchi, Marta Feroci & Leucio Rossi. (2009) Reaction of the Electrogenerated Cyanomethyl Anion with Carbonyl Compounds: A Clean and Safe Synthesis of β-Hydroxynitriles. European Journal of Organic Chemistry 2009:23, pages 3863-3866.
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Jaan PestiChien-Kuang ChenLori SpanglerAlbert J. DelMonteSerge BenoitDerek BerglundJeffrey BienPaul BrodfuehrerYeung ChanElisabeth CorbettCarrie CostelloPaul DeMenaRobert P. DiscordiaWendel DoubledayZhinong GaoStephane GingrasJohn GrossoOscar HaasDavid KacsurChiajen LaiSimon LeungMelanie MillerJale MuslehiddinogluNina NguyenJun QiuMartina OlzogEmily ReiffDominique ThoravalMichael TotlebenDale VanyoPurushotham VemishettiJohn WasylakChenkou Wei. (2009) The Process Development of Ravuconazole: An Efficient Multikilogram Scale Preparation of an Antifungal Agent. Organic Process Research & Development 13:4, pages 716-728.
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Takuya Uchida, Atsushi Somada, Yoshiko Kagoshima, Toshiyuki Konosu & Sadao Oida. (2008) Carbon analogs of antifungal dioxane-triazole derivatives: Synthesis and in vitro activities. Bioorganic & Medicinal Chemistry Letters 18:24, pages 6538-6541.
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Hossein Naeimi & Mohsen Moradian. (2006) Metal(II) Schiff base complexes as catalysts for the high-regioselective conversion of epoxides to β-hydroxy nitriles in glycol solvents. Canadian Journal of Chemistry 84:11, pages 1575-1579.
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M. North. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 621 655 .

James A. Ciaccio, Michael Smrtka, William A. Maio & David Rucando. (2004) Synthesis of β-hydroxy nitriles and 1,3-amino alcohols from epoxides using acetone cyanohydrin as a LiCN precursor. Tetrahedron Letters 45:39, pages 7201-7204.
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Kazuishi Makino & Yoshitaka Ichikawa. (1998) Synthesis of a 2-deoxy-ribose type 1-N-iminosugar. Tetrahedron Letters 39:45, pages 8245-8248.
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A. TSURUOKA, S. NEGI, M. YANAGISAWA, K. NARA, T. NAITO & N. MINAMI. (2010) ChemInform Abstract: Practical Oxirane Ring Opening with in situ Prepared LiCN; Synthesis of (2S,3R)‐3‐(2,4‐Difluorophenyl)‐3‐hydroxy‐2‐methyl‐4‐ (1H‐1,2,4‐triazol‐1‐yl)‐1‐butanenitrile.. ChemInform 29:1.
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Practical Oxirane Ring Opening with In Situ Prepared LiCN; Synthesis of (2S,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)-1-butanenitrile

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Practical Oxirane Ring Opening with In Situ Prepared LiCN; Synthesis of (2S,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)-1-butanenitrile

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