Special Issue

Akira Suzuki's Special Issues, Vol. 80, No. 2, 2010

67 data found. 61 - 67 listedFirst Previous
Paper | Special issue | Vol 80, No. 2, 2010, pp. 1429 - 1448
Published online: 21st December, 2009
DOI: 10.3987/COM-09-S(S)135
Divergent Synthesis of 2,3,5-Substituted Thiophenes by C-H Activation/Borylation/Suzuki Coupling

Venkata A. Kallepalli, Luis Sánchez, Hao Li, Nathan J. Gesmundo, Clarissa L. Turton, Robert E. Maleczka, Jr.,* and Milton R. Smith, III*

*Department of Chemistry, Michigan State University, East Lansing, MI 48824-1322, U.S.A.


C–H activation/borylation has been married with Suzuki coupling to prepare DuP 697 (1) and analogs that would be otherwise difficult to obtain via the traditional synthetic route to 1.

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Note | Special issue | Vol 80, No. 2, 2010, pp. 1449 - 1456
Published online: 4th September, 2009
DOI: 10.3987/COM-09-S(S)50
Stereoselective Preparation of Oxygenated Heterocycles Using Stereocontrolled Tandem Double-Allylation of Carbonyl Compounds with a Boron-Silicon Reagent

Umakanthan Sivasubramaniam and Dennis G. Hall*

*Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada


A one-pot three-component reaction between carbonyl double-allylation reagent 1 and aldehydes was optimized to provide a high diastereoselectivity in the formation of all-cis trisubstituted tetrahydrofurans. A similar procedure applied to dicarbonyl substrates provided an oxabicyclic compound embedding an 8-membered medium ring.

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Note | Special issue | Vol 80, No. 2, 2010, pp. 1457 - 1461
Published online: 15th September, 2009
DOI: 10.3987/COM-09-S(S)72
Tetrahydroquinazoline Derivatives by Aza Diels-Alder Reaction

Giuseppe Cremonesi, Piero Dalla Croce,* Maddalena Gallanti, and Concetta La Rosa

*Department of Organic and Industrial Chemistry, Faculty of Pharmacy, University of Milano, Via Venezian 21, I-20133 Milano, Italy


The reaction of N-(2-Chloromethylphenyl)benzenesulfonamides (1) with N-benzylideneamines (2) gives 1,2,3,4-tetrahydroquinazoline derivatives (3) via the highly reactive o-azaxylylene intermediates. The structure of (3) is fully assigned on the basis of analytical and spectroscopic data. The chemical behaviour of (3) has been studied.

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Note | Special issue | Vol 80, No. 2, 2010, pp. 1463 - 1469
Published online: 9th September, 2009
DOI: 10.3987/COM-09-S(S)95
A Short Access to Chiral Non-Racemic Oxa- and Azaheterocycles by Cross-Metathesis and Pd-Catalyzed Cyclization Sequence

Jun'ichi Uenishi* and Yogesh S. Vikhe

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan


A concise synthesis of chiral non-racemic 2-(3-benzoyloxyprop-1-enyl)tetrahydrofuran (5a), tetrahydropyran (5b), and piperidine (8) is described. Cross-metathesis of optically pure (S)-1-O-benzoyl-3-butene-1,2-diol (2) with protected 4-pentenol, 5-hexenol, and 5-hexenylamine gave the corresponding allyl alcohols (3a), (3b), and (7) in one step, respectively. PdCl2(MeCN)2 catalyzed cyclization of 4a, 4b, and 7 afforded 5a, 5b, and 8 in excellent yields with high enantiomeric purity.

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Note | Special issue | Vol 80, No. 2, 2010, pp. 1471 - 1477
Published online: 24th September, 2009
DOI: 10.3987/COM-09-S(S)106
Gaudichaudysolin A, a New Limonoid from the Bark of Dysoxylum gaudichaudianum

Yuta Nagakura, Reiko Yamanaka, Yusuke Hirasawa, Takahiro Hosoya, Abdul Rahman, Idha Kusumawati, Noor Cholies Zaini, and Hiroshi Morita*

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


A new limonoid, gaudichaudysolin A (1) was isolated from the bark of Dysoxylum gaudichaudianum (Meliaceae) and the structure was elucidated by spectroscopic analysis.

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Note | Special issue | Vol 80, No. 2, 2010, pp. 1479 - 1488
Published online: 15th September, 2009
DOI: 10.3987/COM-09-S(S)107
Oxidative Dimerization of 4-Methoxynaphthylamines in the Presence of Semiconductors

Tetsuya Takeya,* Yosuke Takahashi, Iwao Okamoto, and Osamu Tamura*

*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


Three types of 4-methoxynaphthylamines 4a-c were oxidized by treatment with metal oxides under molecular oxygen (O2). 4-Methoxy-1-naphthylamine 4a and 4,6-dimethoxy-1-naphthylamine 4b, on treatment with TiO2 under O2, gave mainly 2-amino-1,4-naphthoquinone derivatives 5a and 5b, respectively whereas 4,8-dimethoxy-1-naphthylamine 4c afforded an unique carbazole 6c as the major product.

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Note | Special issue | Vol 80, No. 2, 2010, pp. 1489 - 1503
Published online: 20th November, 2009
DOI: 10.3987/COM-09-S(S)133
The Mukaiyama Aldol and Mukaiyama–Michael Reactions Promoted by Commercially Available Molecular Sieves

Masahiro Anada, Takuya Washio, Yudai Watanabe, and Shunichi Hashimoto*

*Laboratory of Synthetic and Industrial Chemistry, Graduate School of Life Science, Division of Life Science, Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12, Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


The Mukaiyama aldol reaction of silyl ketene acetals with aldehydes has been effected by using commercially available 4Å molecular sieves (4Å MS) as a promoter. Various silyl ketene acetals and silyl enol ethers have been shown to be effective nucleophiles for this reaction. For the first time, it has been found that 4Å MS can promote the Mukaiyama–Michael addition reactions of silyl ketene acetals to α,β-enones.

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