Enantioselective cobalt-catalyzed [6+2] cycloadditions of cycloheptatriene with alkynes

被引：44
作者：
Toselli, Nicolas [1 ]
Martin, David [1 ]
Achard, Mathieu [1 ]
Tenaglia, Alphonse [1 ]
Buergi, Thomas [2 ]
Buono, Gerard [1 ]
机构：
[1] Univ Paul Cezanne, CNRS, UMR 6180 Chirotechnol, Lab Synth Asymet, F-13397 Marseille, France
[2] Univ Neuchatel, Inst Chim, CH-2007 Neuchatel, Switzerland
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 02期
关键词：
cobalt; cycloaddition reactions; enantioselective catalysis; phosphoramidites; vibrational circular dichroism;
D O I：
10.1002/adsc.200700424
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The enantioselective cobalt-catalyzed [6+ 2] cycloadditions of cycloheptatriene 1 with alkynes 2 is reported. Chiral phosphoramidites based on 3,3'-disubstituted (R)-BINOL appeared to be efficient ligands, affording the corresponding cycloadducts with good yields and up to 92% ee. A vibrational circular dichroism study afforded the absolute configuration of new chiral (+)-(1S,6R)-7-phenyl[4.2.1]bicyclononatriene 3a and (-)-(1S,6R)-7-trimethylsilyl[4.2.1]bicyclononatriene 3c.
引用
收藏
页码：280 / 286
页数：7
相关论文
共 45 条
  • [1] Cobalt(I)-catalyzed [6+2] cycloadditions of cyclooctatetra(tri)ene with alkynes
    Achard, M
    Mosrin, M
    Tenaglia, A
    Buono, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (07) : 2907 - 2910
  • [2] First cobalt(I)-catalyzed [6+2] cycloadditions of cycloheptatriene with alkynes
    Achard, M
    Tenaglia, A
    Buono, G
    [J]. ORGANIC LETTERS, 2005, 7 (12) : 2353 - 2356
  • [3] [Anonymous], RUSS CHEM REV
  • [4] Enantioselective catalysis using phosphorus-donor ligands containing two or three P-N or P-O bonds
    Ansell, J
    Wills, M
    [J]. CHEMICAL SOCIETY REVIEWS, 2002, 31 (05) : 259 - 268
  • [5] Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects
    Arnold, LA
    Imbos, R
    Mandoli, A
    de Vries, AHM
    Naasz, R
    Feringa, BL
    [J]. TETRAHEDRON, 2000, 56 (18) : 2865 - 2878
  • [6] A MOLYBDENUM-CENTRED (6+2)-PI ADDITION OF ALKYNES TO CYCLOOCTATETRAENE AND CYCLOHEPTATRIENE - STRUCTURAL EVIDENCE FOR AN ARRESTED 1,3-HYDROGEN SHIFT
    BOURNER, DG
    BRAMMER, L
    GREEN, M
    MORAN, G
    ORPEN, AG
    REEVE, C
    SCHAVERIEN, CJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (20) : 1409 - 1411
  • [7] The absolute configuration of heptahelicene:: a VCD spectroscopy study
    Bürgi, T
    Urakawa, A
    Behzadi, B
    Ernst, KH
    Baiker, A
    [J]. NEW JOURNAL OF CHEMISTRY, 2004, 28 (03) : 332 - 334
  • [8] METAL-MEDIATED [6+2]-CYCLOADDITIONS OF ALKYNES TO CYCLOHEPTATRIENE AND N-CARBETHOXYAZEPINE
    CHAFFEE, K
    HUO, P
    SHERIDAN, JB
    BARBIERI, A
    AISTARS, A
    LALANCETTE, RA
    OSTRANDER, RL
    RHEINGOLD, AL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) : 1900 - 1907
  • [9] PHOTOINDUCED [6 + 2] CYCLOADDITIONS OF ALKYNES TO TRICARBONYL(CYCLOHEPTATRIENE)CHROMIUM(0)
    CHAFFEE, K
    SHERIDAN, JB
    AISTARS, A
    [J]. ORGANOMETALLICS, 1992, 11 (01) : 18 - 19
  • [10] Metal-mediated tandem [6+2],homo[6+2] cycloadditions of alkynes to cycloheptatriene. Generation of novel tetracycloundecadienes
    Chen, WC
    Chaffee, K
    Chung, HJ
    Sheridan, JB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (41) : 9980 - 9981
12345