New nitrogen containing chiral diselenides: synthesis and asymmetric addition reactions to olefins
作者： Marcello Tiecco , Lorenzo Testaferri , Claudio Santi , Cristina Tomassini , Francesca Marini
DOI: 10.1016/S0957-4166(00)00469-9
关键词:
摘要: Abstract A simple synthesis of two new nitrogen containing diselenides, 7 and 8 , is described. These compounds were employed as starting materials to effect the asymmetric methoxyselenenylation, hydroxyselenenylation well cyclofunctionalization olefins. Starting from all these addition processes occurred with good facial selectivity. Poor results however obtained . One-pot selenenylation–elimination sequences using catalytic amounts diselenide have also been investigated.
elsevier.com
sci-hub.se 参考文章(26)
Marcello Tiecco, Electrophilic Selenium, Selenocyclizations ChemInform. ,vol. 31, pp. 7- 54 ,(2000) , 10.1007/3-540-48171-0_2
Yoshiaki Nishibayashi, Jai Deo Singh, Yasuyoshi Arikawa, Sakae Uemura, Masanobu Hidai, Rhodium(I)-, iridium(I)-, and ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using diferrocenyl dichalcogenides as chiral ligands Journal of Organometallic Chemistry. ,vol. 531, pp. 13- 18 ,(1997) , 10.1016/S0022-328X(96)06681-8
Thomas Wirth, Gianfranco Fragale, Martin Spichty, Mechanistic Course of the Asymmetric Methoxyselenenylation Reaction Journal of the American Chemical Society. ,vol. 120, pp. 3376- 3381 ,(1998) , 10.1021/JA974177D
Yoshiaki Nishibayashi, Kyohei Segawa, Jai Deo Singh, Shin-ichi Fukuzawa, Kouichi Ohe, Sakae Uemura, Novel Chiral Ligands, Diferrocenyl Dichalcogenides and Their Derivatives, for Rhodium- and Iridium-Catalyzed Asymmetric Hydrosilylation Organometallics. ,vol. 15, pp. 370- 379 ,(1996) , 10.1021/OM950533U
Thomas G. Back, Brian P. Dyck, Masood Parvez, 1,3-Diselenetanes and 1,3-Dithietanes Derived from Camphor. Formation, Structure, Stereochemistry, and Oxidation to Selenoxide and Sulfoxide Products Journal of Organic Chemistry. ,vol. 60, pp. 703- 710 ,(1995) , 10.1021/JO00108A038
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
Shin-ichi Fukuzawa, Kaoru Takahashi, Hirohisa Kato, Hiroshi Yamazaki, Asymmetric Methoxyselenenylation of Alkenes with Chiral Ferrocenylselenium Reagents Journal of Organic Chemistry. ,vol. 62, pp. 7711- 7716 ,(1997) , 10.1021/JO970982Z
Ken-ichi Fujita, Kazuhisa Murata, Michio Iwaoka, Shuji Tomoda, Asymmetric methoxyselenenylation of olefins using an optically active diaryl diselenide derived from d-mannitol Tetrahedron Letters. ,vol. 36, pp. 5219- 5222 ,(1995) , 10.1016/0040-4039(95)00976-J
Thomas Wirth, Organoselenium Chemistry in Stereoselective Reactions Angewandte Chemie. ,vol. 39, pp. 3740- 3749 ,(2000) , 10.1002/1521-3773(20001103)39:21<3740::AID-ANIE3740>3.0.CO;2-N
Yoshiaki Nishibayashi, Jai Deo Singh, Sakae Uemura, Shin-ichi Fukuzawa, Synthesis of chiral diferrocenyl diselenides and their application to asymmetric reactions Tetrahedron Letters. ,vol. 35, pp. 3115- 3118 ,(1994) , 10.1016/S0040-4039(00)76844-4