Asymmetric Ylide Reactions: Epoxidation, Cyclopropanation, Aziridination, Olefination, and Rearrangement
About: This article is published in Chemical Reviews.The article was published on 1997-10-01. It has received 717 citations till now. The article focuses on the topics: Cyclopropanation & Ylide.
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TL;DR: This review will focus mainly on the new methods that have appeared in the literature since 1989 for stereoselective cyclopropanation reactions from olefins: the halomethylmetal-mediated cycloalkane reactions, the transition metal-catalyzed decomposition of diazo compounds, and the nucleophilic addition-ring closure sequence.
Abstract: Organic chemists have always been fascinated by the cyclopropane subunit.1 The smallest cycloalkane is found as a basic structural element in a wide range of naturally occurring compounds.2 Moreover, many cyclopropane-containing unnatural products have been prepared to test the bonding features of this class of highly strained cycloalkanes3 and to study enzyme mechanism or inhibition.4 Cyclopropanes have also been used as versatile synthetic intermediates in the synthesis of more functionalized cycloalkanes5,6 and acyclic compounds.7 In recent years, most of the synthetic efforts have focused on the enantioselective synthesis of cyclopropanes.8 This has remained a challenge ever since it was found that the members of the pyrethroid class of compounds were effective insecticides.9 New and more efficient methods for the preparation of these entities in enantiomerically pure form are still evolving, and this review will focus mainly on the new methods that have appeared in the literature since 1989. It will elaborate on only three types of stereoselective cyclopropanation reactions from olefins: the halomethylmetal-mediated cyclopropanation reactions (eq 1), the transition metal-catalyzed decomposition of diazo compounds (eq 2), and the nucleophilic addition-ring closure sequence (eqs 3 and 4). These three processes will be examined in the context of diastereoand enantiocontrol. In the last section of the review, other methods commonly used to make chiral, nonracemic cyclopropanes will be briefly outlined.
1,426 citations
1,092 citations
TL;DR: This paper presents results of aalysis experiment conducted at the Dalian Institute of Chemical Physics of Chinese Academy of Sciences (Dalian 116023) and Jingmen Technological College (Jingmen 448000) using gas chromatography for the recovery of Na6(CO3) from Na2SO4.
Abstract: Laboratory for Advanced Materials and New Catalysis, School of Chemistry and Materials Science, Hubei University, Wuhan 430062, China,Laboratory of Natural Gas Utilization and Applied Catalysis, Dalian Institute of Chemical Physics of Chinese Academy of Sciences, Dalian 116023,China, and Jingmen Technological College, Jingmen 448000, ChinaReceived June 30, 2004
864 citations
772 citations
TL;DR: Odd-electron, redox-active ligands are discussed in the context of catalysis and their participation in catalytic processes and related stoichiometric transformations are discussed.
Abstract: Odd-electron, redox-active ligands are discussed in the context of catalysis. We focus on ligand-based, non-singlet state intermediates and their participation in catalytic processes and related stoichiometric transformations.
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3,393 citations
Book•
13 Aug 1993
TL;DR: Asymmetric Hydrogenation (T. Ohkuma, et al. as discussed by the authors ), asymmetric carbon-Carbon Bond-Forming Reactions (K. Nozaki & I. Negishi). Asymmetric Addition and Insertion Reactions of Catalytically-Generated Metal Carbenes (M. O'Donnell), and asymptotic phase-transfer Reactions.
Abstract: Asymmetric Hydrogenation (T. Ohkuma, et al.). Asymmetric Hydrosilylation and Related Reactions (H. Nishiyama & K. Itoh). Asymmetric Isomerization of Allylamines (S. Akutagawa, et al.). Asymmetric Carbometallations (E. Negishi). Asymmetric Addition and Insertion Reactions of Catalytically-Generated Metal Carbenes (M. Doyle). Asymmetric Oxidations and Related Reactions (R. Johnson, et al.). Asymmetric Carbonylations (K. Nozaki & I. Ojima). Asymmetric Carbon-Carbon Bond-Forming Reactions (K. Maruoka, et al.). Asymmetric Amplification and Autocatalysis (K. Soai & T. Shibata). Asymmetric Phase-Transfer Reactions (M. O'Donnell). Asymmetric Polymerization (Y. Okamoto & T. Nakano). Epilogue. Appendix. Index.
2,758 citations
1,005 citations
Book•
01 Jan 1994
TL;DR: In this article, Zade et al. present a list of functional groups containing selenium and tellurium and some that are not known and some of which are biologically relevant small molecules containing them.
Abstract: 1 Synthesis of organoselenium compounds 1 Sanjio S. Zade and Harkesh B. Singh 2 Synthesis of organotellurium compounds 181 Sanjio S. Zade and Harkesh B. Singh 3 NMR of organoselenium and organotellurium compounds 277 Arunashree Panda and Harkesh B. Singh 4 Advances in the photochemistry of organoselenium and organotellurium compounds 447 Akihiko Ouchi, Wataru Ando, and Makoto Oba 5 Rearrangements of organoselenium and organotellurium compounds 543 Osamu Niyomura and Toshiaki Murai 6 Electrophilic selenium/tellurium reagents: Reactivity and their contribution to Green Chemistry 569 Claudio Santi and Caterina Tidei 7 Synthesis of selenium and tellurium ylides and carbanions. Application to organic synthesis 657 Joao V. Comasseto, Leandro Piovan, and Edison P. Wendler 8 Organic conductors containing selenium and tellurium 735 Filipe Vilela, Zuzana Vobecka, and Peter J. Skabara 9 Organic diselenides, ditellurides, polyselenides and polytellurides. Synthesis and reactions 765 Vladimir A. Potapov 10 Organic selenocyanates, tellurocyanates and related compounds 845 Akio Toshimitsu 11 Recent advances of structural chemistry of organoselenium and organotellurium compounds 885 Waro Nakanishi, Satoko Hayashi, Masato Hashimoto, Massimiliano Arca, Maria Carla Aragoni, and Vito Lippolis 12 Supramolecular architectures based on M(lone pair) * * * (arene) interactions for M=Se and Te 973 Ignez Caracelli, Ionel Haiduc, Julio Zukerman-Schpector, and Edward R. T. Tiekink 13 Synthesis of biologically relevant small molecules containing selenium. Part A. Antioxidant compounds 989 Antonio L. Braga and Jamal Rafique 14 Synthesis of biologically relevant small molecules containing selenium. Part B. Anti-infective and anticancer compounds 1053 Antonio L. Braga and Jamal Rafique 15 Synthesis of biologically relevant small molecules containing selenium. Part C. Miscellaneous biological activities 1119 Antonio L. Braga and Jamal Rafique 16 Enzyme mimetic chemistry of organoselenium compounds 1175 Debasish Bhowmick and Govindasamy Mugesh 17 Selenium and tellurium derivatives of carbohydrates and nucleotides 1237 Anna Maciaszek, Agnieszka Tomaszewska, and Piotr Guga 18 Selenium and tellurium heterocycles 1279 Margaret E. Logan, Meredith A. Lang, and Michael R. Detty 19 Recent advances in the insertion and extrusion reactions of selenium and tellurium in organic compounds 1361 Frank S. Guziec, Jr. and Lynn James Guziec 20 Organic compounds containing bonds between Se or Te with P, As, Sb and Bi 1401 Toshiaki Murai 21 Coordination chemistry of organoselenium and organotellurium compounds 1433 Yuichiro Mutoh 22 Positively charged selenium- and tellurium-stabilized species 1501 Soichi Sato 23 A summary of functional groups containing selenium and tellurium: A catalog of the many groups that are known and some that are not 1515 Janet E. Hack and Joel F. Liebman Author index 1523 Subject index
627 citations
610 citations