共 26 条
Asymmetric intramolecular arylcyanation of unactivated Olefins via C-CN bond activation
被引:188
作者:

Watson, Mary P.
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

Jacobsen, Eric N.
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
机构:
[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
关键词:
D O I:
10.1021/ja805094j
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
The enantioselective, intramolecular arylcyanation of unactivated olefins via C-CN bond activation has been accomplished using a Ni (0) catalyst and BPh3 co-catalyst. High enantioselectivities are achieved using TangPHOS as a chiral ligand. This method allows the generation of two new C-C bonds and one new quaternary carbon stereogenic center in a single synthetic step, converting readily available benzonitrile substrates into 1,1-disubstituted indanes in 49-85% yield and 92-97% ee.
引用
收藏
页码:12594 / +
页数:3
相关论文
共 26 条
- [1] Experimental and theoretical examination of C-CN bond activation of benzonitrile using zerovalent nickel[J]. ORGANOMETALLICS, 2008, 27 (15) : 3811 - 3817Atesin, Tuelay A.论文数: 0 引用数: 0 h-index: 0机构: Univ Rochester, Dept Chem, Rochester, NY 14627 USALi, Ting论文数: 0 引用数: 0 h-index: 0机构: Univ Rochester, Dept Chem, Rochester, NY 14627 USALachaize, Sebastien论文数: 0 引用数: 0 h-index: 0机构: Univ Rochester, Dept Chem, Rochester, NY 14627 USAGarcia, Juventino J.论文数: 0 引用数: 0 h-index: 0机构: Univ Rochester, Dept Chem, Rochester, NY 14627 USAJones, William D.论文数: 0 引用数: 0 h-index: 0机构: Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA
- [2] Asymmetric, catalytic synthesis of α-chiral amines using a novel bis(phosphine) monoxide chiral ligand[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) : 14260 - 14261Boezio, AA论文数: 0 引用数: 0 h-index: 0机构: Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, CanadaPytkowicz, J论文数: 0 引用数: 0 h-index: 0机构: Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, CanadaCôté, A论文数: 0 引用数: 0 h-index: 0机构: Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, CanadaCharette, AB论文数: 0 引用数: 0 h-index: 0机构: Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
- [3] PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) : 10125 - 10138BURK, MJ论文数: 0 引用数: 0 h-index: 0机构: DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880 DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880FEASTER, JE论文数: 0 引用数: 0 h-index: 0机构: DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880 DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880NUGENT, WA论文数: 0 引用数: 0 h-index: 0机构: DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880 DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880HARLOW, RL论文数: 0 引用数: 0 h-index: 0机构: DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880 DUPONT CO INC,CENT RES & DEV EXPTL STN,WILMINGTON,DE 19880
- [4] PREPARATION OF ENANTIOMERICALLY PURE (R,R)-BozPHOS [(2R,5R)-1-{2-[(2R,5R)-2,5-dimethylphospholan-1-yl] phenyl}2,5-dimethylphospholane 1-oxide][J]. ORGANIC SYNTHESES, 2006, 83 : 1 - +Cote, Alexandre论文数: 0 引用数: 0 h-index: 0机构: Univ Montreal, Dept Chim, POB 6128,Stn Downtown, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chim, POB 6128,Stn Downtown, Montreal, PQ H3C 3J7, CanadaDesrosiers, Jean-Nicolas论文数: 0 引用数: 0 h-index: 0机构: Univ Montreal, Dept Chim, POB 6128,Stn Downtown, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chim, POB 6128,Stn Downtown, Montreal, PQ H3C 3J7, CanadaBoezio, Alessandro A.论文数: 0 引用数: 0 h-index: 0机构: Univ Montreal, Dept Chim, POB 6128,Stn Downtown, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chim, POB 6128,Stn Downtown, Montreal, PQ H3C 3J7, CanadaCharette, Andre B.论文数: 0 引用数: 0 h-index: 0机构: Univ Montreal, Dept Chim, POB 6128,Stn Downtown, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chim, POB 6128,Stn Downtown, Montreal, PQ H3C 3J7, Canada
- [5] Catalytic asymmetric synthesis of all-carbon quaternary stereocenters[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5363 - 5367Douglas, CJ论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USAOverman, LE论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
- [6] Cleavage of carbon-carbon bonds in aromatic nitriles using nickel(0)[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) : 9547 - 9555Garcia, JJ论文数: 0 引用数: 0 h-index: 0机构: Univ Rochester, Dept Chem, Rochester, NY 14627 USABrunkan, NM论文数: 0 引用数: 0 h-index: 0机构: Univ Rochester, Dept Chem, Rochester, NY 14627 USAJones, WD论文数: 0 引用数: 0 h-index: 0机构: Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA
- [7] Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 336 - 345Helmchen, G论文数: 0 引用数: 0 h-index: 0机构: Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany论文数: 引用数: h-index:机构:
- [8] Lewis acids accelerate reductive elimination of RCN from P2Pd(R)(CN)[J]. ORGANOMETALLICS, 1999, 18 (03) : 297 - 299Huang, JK论文数: 0 引用数: 0 h-index: 0机构: Dupont Co, Dept Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USAHaar, CM论文数: 0 引用数: 0 h-index: 0机构: Dupont Co, Dept Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USANolan, SP论文数: 0 引用数: 0 h-index: 0机构: Dupont Co, Dept Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USAMarcone, JE论文数: 0 引用数: 0 h-index: 0机构: Dupont Co, Dept Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USAMoloy, KG论文数: 0 引用数: 0 h-index: 0机构: Dupont Co, Dept Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
- [9] Intramolecular cyanoamidation of unsaturated cyanoformamides catalyzed by palladium: an efficient synthesis of multi-functionalized lactams[J]. TETRAHEDRON, 2007, 63 (14) : 2978 - 2989Kobayashi, Yusuke论文数: 0 引用数: 0 h-index: 0机构: Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, JapanKamisaki, Haruhi论文数: 0 引用数: 0 h-index: 0机构: Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, JapanTakeda, Hiroshi论文数: 0 引用数: 0 h-index: 0机构: Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, JapanYasui, Yoshizumi论文数: 0 引用数: 0 h-index: 0机构: Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, JapanYanada, Reiko论文数: 0 引用数: 0 h-index: 0机构: Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, JapanTakemoto, Yoshiji论文数: 0 引用数: 0 h-index: 0机构: Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
- [10] Palladium-catalyzed intramolecular cyanoamidation of alkynyl and alkenyl cyanoformamides[J]. ORGANIC LETTERS, 2006, 8 (13) : 2711 - 2713Kobayashi, Yusuke论文数: 0 引用数: 0 h-index: 0机构: Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, JapanKamisaki, Haruhi论文数: 0 引用数: 0 h-index: 0机构: Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, JapanYanada, Reiko论文数: 0 引用数: 0 h-index: 0机构: Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan论文数: 引用数: h-index:机构: