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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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
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.
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Dr. Woo-Jin Yoo, Arata Tanoue and Prof. Dr. Shū Kobayashi
Article first published online: 21 AUG 2014 | DOI: 10.1002/ajoc.201402108
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.
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Dr. Liang Wang, Yuye Chen and Prof. Jian Xiao
Article first published online: 21 AUG 2014 | DOI: 10.1002/ajoc.201402093
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.
- 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
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.
- Decarboxylative CP 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
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.