Chiral Diene-Phosphine Tridentate Ligands for Rhodium-Catalyzed Asymmetric Cycloisomerization of 1,6-Enynes

被引：58
|
作者：
Nishimura, Takahiro [1 ]
Maeda, Yuko [1 ]
Hayashi, Tamio [1 ]
机构：
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 14期
关键词：
NITROGEN-BRIDGED 1,6-ENYNES; GOLD(I)-CATALYZED CYCLOISOMERIZATION; ENANTIOSELECTIVE SYNTHESIS; CYCLOHEXADIENYL ALKYNES; CONJUGATE ADDITION; STEERING LIGANDS; ENYNES; COMPLEXES; PLATINUM; CYCLIZATION;
D O I：
10.1021/ol2013236
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric cycloisomerization of nitrogen-bridged 1,6-enynes proceeded in the presence of a cationic rhodium complex coordinated with a chiral diene/phosphine tridentate ligand to give high yields of chiral 3-azabicyclo[4.1.0]heptenes with high enantioselectivity.
引用
收藏
页码：3674 / 3677
页数：4
相关论文
共 50 条
  • [41] The gold(I)-catalyzed cycloisomerization of 1,6-enynes to 1,4-dienes
    Lee, Sang Ick
    Kim, Soo Min
    Kim, Sun Young
    Chung, Young Keun
    SYNLETT, 2006, (14) : 2256 - 2260
  • [42] Chiral phosphine-olefin ligands in the rhodium-catalyzed asymmetric 1,4-addition reactions
    Duan, Wei-Liang
    Iwamura, Hiroshi
    Shintani, Ryo
    Hayashi, Tamio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) : 2130 - 2138
  • [43] RHODIUM-CATALYZED ASYMMETRIC HYDROFORMYLATION WITH CHIRAL DIPHOSPHITE LIGANDS
    BUISMAN, GJH
    KAMER, PCJ
    VANLEEUWEN, PWNM
    TETRAHEDRON-ASYMMETRY, 1993, 4 (07) : 1625 - 1634
  • [44] A Highly Reusable Rhodium Catalyst-Organic Framework for the Intramolecular Cycloisomerization of 1,6-Enynes
    Corkum, Elizabeth G.
    Hass, Michael J.
    Sullivan, Andrew D.
    Bergens, Steven H.
    ORGANIC LETTERS, 2011, 13 (13) : 3522 - 3525
  • [45] Enantioselective Platinum-Catalyzed Tandem Hydroarylation-Cycloisomerization of 1,6-Enynes
    Toullec, Patrick Yves
    Chao, Chung-Meng
    Chen, Qian
    Gladiali, Serafino
    Genet, Jean-Pierre
    Michelet, Veronique
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) : 2401 - 2408
  • [46] Rhodium-catalyzed cyclization reaction of 1,6-enynes with arylboronic acids through β-hydride elimination/hydrorhodation sequence
    Shimada, Masahiko
    Harumashi, Tatsuro
    Miura, Tomoya
    Murakami, Masahiro
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (06) : 1035 - 1040
  • [47] Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones
    Nishimura, Takahiro
    Guo, Xun-Xiang
    Uchiyama, Nanase
    Katoh, Taisuke
    Hayashi, Tamio
    Journal of the American Chemical Society, 2008, 130 (05): : 1576 - 1577
  • [48] Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones
    Nishimura, Takahiro
    Guo, Xun-Xiang
    Uchiyama, Nanase
    Katoh, Taisuke
    Hayashi, Tamio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (05) : 1576 - +
  • [49] Rhodium-catalyzed reductive cyclization of 1,6-enynes and stereoselective synthesis of the putative structure of lucentamycin A and its stereoisomers
    Ham, Young Jin
    Yu, Hana
    Kim, Nam Doo
    Hah, Jung-Mi
    Selim, Khalid B.
    Choi, Hwan Geun
    Sim, Taebo
    TETRAHEDRON, 2012, 68 (07) : 1918 - 1925
  • [50] Thiazole, Imidazole and Oxazoline Based N,P-Ligands for Palladium-Catalyzed Cycloisomerization of 1,6-Enynes
    Quan, Xu
    Liu, Jianguo
    Rabten, Wangchuk
    Diomedi, Simone
    Singh, Thishana
    Andersson, Pher G.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (20) : 3427 - 3433
12345