Enantioselective Pd-catalyzed C*-C, C*-N, and C*-S bond formation reactions using first P,P,N,N-tetradentate chiral phosphites

被引:12
作者
Tsarev, VN
Konkin, SI
Shyryaev, AA
Davankov, VA
Gavrilov, KN
机构
[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
[2] Ryazan State Pedag Univ, Dept Chem, Ryazan 390000, Russia
基金
俄罗斯基础研究基金会;
关键词
D O I
10.1016/j.tetasy.2005.04.010
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral P.P,N.N-tetradentate ferrocene-derived iminophosphite and iminodiamidophosphite ligands were synthesized for the first time. The applicability of these ligands in asymmetric C*-C, C*-N, and C*-S bond formation was demonstrated. High enantioselectivity was obtained in the Pd-catalyzed allylic substitution Of 1,3-diphenylallyl acetate with dimethyl malonate (tip to 90% ee), pyrrolidine (up to 85% ee), and sodium para-toluene sulfinate (LIP to 81%), with the iminodiamidophosphite ligand being the best stereoselector. (C) 2005 Published by Elsevier Ltd.
引用
收藏
页码:1737 / 1741
页数:5
相关论文
共 50 条
[41]   A Practical Synthesis of Indoles via a Pd-Catalyzed C-N Ring Formation [J].
Vaswani, Rishi G. ;
Albrecht, Brian K. ;
Audia, James E. ;
Cote, Alexandre ;
Dakin, Les A. ;
Duplessis, Martin ;
Gehling, Victor S. ;
Harmange, Jean-Christophe ;
Hewitt, Michael C. ;
Leblanc, Yves ;
Nasveschuk, Christopher G. ;
Taylor, Alexander M. .
ORGANIC LETTERS, 2014, 16 (16) :4114-4117
[42]   Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C-N/C-S Bond Formation in Allylic Surrogates [J].
Deng, Lei ;
Kleij, Arjan W. ;
Yang, Weibo .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (72) :19156-19161
[43]   Cu/Pd cooperatively catalyzed tandem C-N and C-P bond formation: access to phosphorated 2H-indazoles [J].
Wei, Weiwei ;
Li, Xuanyi ;
Gu, Meng ;
Yao, Hequan ;
Lin, Aijun .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (39) :8458-8462
[44]   Molecular basis for the P450-catalyzed C–N bond formation in indolactam biosynthesis [J].
Fei He ;
Takahiro Mori ;
Iori Morita ;
Hitomi Nakamura ;
Miroslava Alblova ;
Shotaro Hoshino ;
Takayoshi Awakawa ;
Ikuro Abe .
Nature Chemical Biology, 2019, 15 :1206-1213
[45]   BippyPhos: A Highly Versatile Ligand for Pd-Catalyzed C-N, C-O and C-C Couplings [J].
Singer, Robert A. .
ISRAEL JOURNAL OF CHEMISTRY, 2020, 60 (3-4) :294-302
[46]   Catalytic Enantioselective Synthesis of N-C Axially Chiral N-(2,6-Disubstituted-phenyl)sulfonamides through Chiral Pd-Catalyzed N-Allylation [J].
Fukasawa, Sota ;
Toyoda, Tatsuya ;
Kasahara, Ryohei ;
Nakamura, Chisato ;
Kikuchi, Yuuki ;
Hori, Akiko ;
Richards, Gary J. ;
Kitagawa, Osamu .
MOLECULES, 2022, 27 (22)
[47]   New C-N and C-C bond forming reactions catalyzed by titanium complexes [J].
Odom, AL .
DALTON TRANSACTIONS, 2005, (02) :225-233
[48]   Iridium(I)-Catalyzed C-C and C-N Bond Formation Reactions via the Borrowing Hydrogen Strategy [J].
Genc, Sertac ;
Arslan, Burcu ;
Gulcemal, Suleyman ;
Gunnaz, Salih ;
Cetinkaya, Bekir ;
Gulcemal, Derya .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10) :6286-6297
[49]   Mechanism of the α,α-diarylprolinol trimethylsilyl ether-catalyzed enantioselective C-C, C-N, C-F, C-S, and C-Br bond forming reactions [J].
Wong, Chiong Teck .
TETRAHEDRON, 2009, 65 (36) :7491-7497
[50]   Exploiting a C-N bond Forming Cytochrome P450 Monooxygenase for C-S Bond Formation [J].
Morita, Iori ;
Mori, Takahiro ;
Mitsuhashi, Takaaki ;
Hoshino, Shotaro ;
Taniguchi, Yoshimasa ;
Kikuchi, Takashi ;
Nagae, Kei ;
Nasu, Norihiro ;
Fujita, Makoto ;
Ohwada, Tomohiko ;
Abe, Ikuro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (10) :3988-3993