Syntheses and Reactions of New Optically Active Terpene Dialkyl Diselenides
作者： Jacek Ścianowski , Zbigniew Rafiński , Andrzej Wojtczak
关键词: Monoterpene 、 Diselenide 、 Diastereomer 、 Organic chemistry 、 Enantioselective synthesis 、 Electrophilic addition 、 Alkyl 、 Bornane 、 Chemistry 、 Terpene
摘要: The reaction of sodium diselenide with optically active alkyl tosylates or chlorides is found to be a useful method for the synthesis dialkyl diselenides. Optically monoterpene diselenides derived from menthane, carane, pinane, and bornane systems have been obtained. influence terpene fragment obtained on diastereomeric excess methoxyselenylation products has investigated. best result was observed (–)-diisopinocamphyl diselenide. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
sci-hub.se 参考文章(46)
Marcello Tiecco, Lorenzo Testaferri, Luana Bagnoli, Valentina Purgatorio, Andrea Temperini, Francesca Marini, Claudio Santi, Efficient asymmetric selenocyclizations of alkenyl oximes into cyclic nitrones and 1,2-oxazines promoted by sulfur containing diselenides Tetrahedron: Asymmetry. ,vol. 12, pp. 3297- 3304 ,(2001) , 10.1016/S0957-4166(02)00013-7
Thomas G. Back, Ziad Moussa, Diselenides and Allyl Selenides as Glutathione Peroxidase Mimetics. Remarkable Activity of Cyclic Seleninates Produced in Situ by the Oxidation of Allyl ω-Hydroxyalkyl Selenides Journal of the American Chemical Society. ,vol. 125, pp. 13455- 13460 ,(2003) , 10.1021/JA0357588
Marcello Tiecco, Lorenzo Testaferri, Claudio Santi, Francesca Marini, Luana Bagnoli, Andrea Temperini, Asymmetric selenomethoxylation of alkenes with camphorselenenyl sulfate Tetrahedron Letters. ,vol. 39, pp. 2809- 2812 ,(1998) , 10.1016/S0040-4039(98)00252-4
Marcello Tiecco, Lorenzo Testaferri, Francesca Marini, Silvia Sternativo, Claudio Santi, Luana Bagnoli, Andrea Temperini, Asymmetric aldol reactions from titanium enolates of α-seleno ketones and esters Tetrahedron-asymmetry. ,vol. 15, pp. 783- 791 ,(2004) , 10.1016/J.TETASY.2003.12.035
Thomas G. Back, Brian P. Dyck, Masood Parvez, Unexpected formation of 1,3-diselenetanes from the reaction of camphor enolate with selenium Journal of The Chemical Society, Chemical Communications. pp. 515- 516 ,(1994) , 10.1039/C39940000515
Marcello Tiecco, Lorenzo Testaferri, Claudio Santi, Cristina Tomassini, Francesca Marini, Luana Bagnoli, Andrea Temperini, New nitrogen containing chiral diselenides: synthesis and asymmetric addition reactions to olefins Tetrahedron-asymmetry. ,vol. 11, pp. 4645- 4650 ,(2000) , 10.1016/S0957-4166(00)00469-9
Thomas G. Back, Siqiao Nan, Asymmetric methoxyselenenylations with camphor-based selenium electrophiles Journal of The Chemical Society-perkin Transactions 1. pp. 3123- 3124 ,(1998) , 10.1039/A806707D
Thomas Wirth, Chiral selenium compounds in organic synthesis Tetrahedron. ,vol. 55, pp. 1- 28 ,(1999) , 10.1016/S0040-4020(98)00946-6
Marcello Tiecco, Lorenzo Testaferri, Claudio Santi, Cristina Tomassini, Francesca Marini, Luana Bagnoli, Andrea Temperini, Asymmetric Azidoselenenylation of Alkenes: A Key Step for the Synthesis of Enantiomerically Enriched Nitrogen-Containing Compounds Angewandte Chemie International Edition. ,vol. 42, pp. 3131- 3133 ,(2003) , 10.1002/ANIE.200351229
H. D. Flack, On enantiomorph‐polarity estimation Acta Crystallographica Section A. ,vol. 39, pp. 876- 881 ,(1983) , 10.1107/S0108767383001762