Asian Journal of Organic Chemistry
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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
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
Give 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.
Recently Published Articles
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Shin Ando, Hirofumi Matsunaga and Tadao Ishizuka
Article first published online: 13 AUG 2014 | DOI: 10.1002/ajoc.201402089
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.
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Article first published online: 12 AUG 2014 | DOI: 10.1002/ajoc.201402088
Go with the ortho: ortho-Nitrobenzoic acids with various functional groups undergo decarboxylative CP 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.
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Wen-Bin Xu, Qing-Hui Xu, Zhen-Fa Zhang and Ji-Zhen Li
Article first published online: 11 AUG 2014 | DOI: 10.1002/ajoc.201402084
Goodnit-rile: A Cu2O-mediated cross coupling of arenediazonium tetrafluoroborates with trimethylsilyl cyanide (TMSCN) to form aromatic nitriles is presented. This method provides appealing and convenient access to aromatic nitriles compared with the traditional Sandmeyer reaction with toxic CuCN via nucleophilic substitution. A variety of functional groups are well tolerated in moderate to high yield in this protocol.
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Article first published online: 11 AUG 2014 | DOI: 10.1002/ajoc.201402123
Concentrate on this one: The Saito photochemical reduction of m-(trifluoromethyl)benzoates has been revisited. In contrast to the conventional conditions, the developed method eliminates the formation of alkene byproducts at high concentrations. Combining direct esterification and the Saito photochemical reduction, a one-pot deoxygenation process of alcohols has also been developed. LED=light-emitting diode; TsOH=4-toluenesulfonic acid.
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Dr. Zhiqiang Ma, Dr. Bin Cheng and Prof. Dr. Hongbin Zhai
Article first published online: 6 AUG 2014 | DOI: 10.1002/ajoc.201402116
It’s got potential: An efficient synthesis of the oxo-bridged 7/6-bicyclic precursor 4 that is potentially useful for the construction of harringtonolide (1) has been realized through a [4+3] cycloaddition reaction as the key transformation.