Asian Journal of Organic Chemistry

Cover image for Vol. 3 Issue 8

Managing Editor: Richard Threlfall; Editorial Board Chairs: Sung Ho Kang, Keiji Maruoka, Deqing Zhang

Impact Factor: 2.292

ISI Journal Citation Reports © Ranking: 2013: 27/58 (Chemistry Organic)

Online ISSN: 2193-5815

Associated Title(s): Advanced Synthesis & Catalysis, Chemistry – An Asian Journal, European Journal of Organic Chemistry

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August 01, 2014

VIP: Synthesis of 19-Nor-Vitamin D A-Ring Synthons via Ring-Closing Olefin Metathesis

Yu Nagai, Tomoe Tanami, Junko Abe, Dr. Hazuki Nagai, Toru Hamamizu, Kaichiro Kominato, Keisuke Iida and Prof. Dr. Kazuo Nagasawa

Synthesis of 19-Nor-Vitamin D A-Ring Synthons via Ring-Closing Olefin MetathesisGive me a D: A synthetic method for making A-ring synthons for 19-nor-vitamin D was developed based on ring-closing olefin metathesis (RCM) with a linear precursor, followed by palladium-catalyzed isomerization of the endocyclic olefin product to give the target exocyclic olefin. PG=protecting group; TBS=tert-butyldimethylsilyl; Tf=trifluoromethanesulfonyl.

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Recently Published Articles

  1. Mother Diamine: A Universal Building Block for Making Chiral Ligands from Daughter Diamines to Binol, Binap and Monophos Analogues

    Ansoo Lee, Dr. Soon Mog So, Dr. Alan J. Lough, Prof. Dr. Hyunwoo Kim and Prof. Dr. Jik Chin

    Article first published online: 26 AUG 2014 | DOI: 10.1002/ajoc.201402135

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    The mother lode: Various chiral ligands, such as vicinal diamines, diols, phosphoramidites, and diphosphines, were readily prepared from a universal building block, “mother diamine” (MD). Tuning of MDphos resulted in enhanced reactivity and selectivity in Rh-catalyzed asymmetric hydrogenation.

  2. Zinc(II) Hexachloroantimonate-Catalyzed Oxidative Allylation of Glycine Derivatives

    Dr. Woo-Jin Yoo, Arata Tanoue and Prof. Dr. Shū Kobayashi

    Article first published online: 21 AUG 2014 | DOI: 10.1002/ajoc.201402108

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    Proof-of-concept for the use of metal antimonates as bifunctional catalysts for oxidative coupling reactions is described. A well-defined zinc(II) antimonate salt enables the α-functionalization of glycine derivatives through a sequential aerobic oxidation-allylation reaction, in which the antimonate anion is responsible for the aerobic oxidation and the zinc cation acts as a Lewis acid for the allylation reaction. EWG=electron-withdrawing group; PMP=p-methoxyphenyl.

  3. Alkylideneindoleninium Ions and Alkylideneindolenines: Key Intermediates for the Asymmetric Synthesis of 3-Indolyl Derivatives

    Dr. Liang Wang, Yuye Chen and Prof. Jian Xiao

    Article first published online: 21 AUG 2014 | DOI: 10.1002/ajoc.201402093

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    Long words, short routes: This Focus Review retrospects the latest advances in catalytic asymmetric synthesis of 3-substituted indoles through alkylideneindoleninium ions and alkylideneindolenine intermediates. Various generation strategies for alkylideneindoleninium ions and alkylideneindolenine intermediates based on different leaving groups and catalytic asymmetric protocols are reviewed. LG = leaving group.

  4. Use of a Desymmetrized meso Molecule as a Chiral Ligand: Development of Chiral N-Heterocyclic Carbene Ligands for Asymmetric Allylic Arylations with Grignard Reagents

    Shin Ando, Hirofumi Matsunaga and Tadao Ishizuka

    Article first published online: 13 AUG 2014 | DOI: 10.1002/ajoc.201402089

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    Broken symmetry: The desymmetrization of a meso molecule was used for the development of a chiral N-heterocyclic carbene (NHC) ligand. The stereocontrol in asymmetric allylic arylations was improved to 89 % ee via derivatization studies. The resultant copper catalyst was effective at the level of 0.05 mol % loading for gram-scale reactions.

  5. Decarboxylative C[BOND]P Coupling of o-Nitrobenzoic Acids with H-Phosphonates

    Junchen Li, Xiaojing Bi, Prof. Hongmei Wang and Prof. Junhua Xiao

    Article first published online: 12 AUG 2014 | DOI: 10.1002/ajoc.201402088

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    Go with the ortho: ortho-Nitrobenzoic acids with various functional groups undergo decarboxylative C[BOND]P coupling with H-phosphonates by using a bimetallic Pd/Ag catalytic system for the preparation of biologically and synthetically important aryl phosphonates. DMF=N,N-dimethylformamide.