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. Synthesis, Physical Properties, and Photocurrent Behavior of Strongly Emissive Boron-Chelate Heterochrysene Derivatives

    Dr. Hailei Zhang, Dr. Xiaozhong Hong, Prof. Xinwu Ba, Bei Yu, Dr. Xin Wen, Dr. Sujuan Wang, Prof. Xuefei Wang, Lei Liu and Prof. Jinchong Xiao

    Article first published online: 1 SEP 2014 | DOI: 10.1002/ajoc.201402131

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    Crysene point: A N,O-chelated boron complex 2 and its analogue 1 have been synthesized and characterized. Single crystal analysis of 1 shows that all carbon and nitrogen atoms are almost in a single plane. 1 and 2 emit green and yellow light in dichloromethane, respectively. The photocurrent response of a 1-single-walled carbon nanotube thin film is steady and reproducible.

  2. Palladium-Catalyzed Desulfinative Iodination of Sodium Sulfinates and Sulfonyl Hydrazides

    Saiwen Liu, Jinjin Chen, Ran Zhang, Feng Zhao and Prof. Dr. Guo-Jun Deng

    Article first published online: 1 SEP 2014 | DOI: 10.1002/ajoc.201402140

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    ‘Tis I: Palladium-catalyzed desulfinative iodination of sodium sulfinates and sulfonyl hydrazides with KI or I2 can be realized under mild reactions using molecular oxygen as the environmentally benign oxidant. The reaction is not sensitive to moisture and is thus very easy to handle. Various functional groups are well tolerated under the optimized reaction conditions. NMP=N-methylpyrrolidone; TFA= trifluoroacetic acid.

  3. 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.

  4. 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.

  5. 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.