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Intramolecular C-H insertion reactions of boroxy Fischer carbene complexes.: Regio- and diastereoselective modification of terpenes
被引:27
作者:

Barluenga, J
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机构: Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada, CSIC, E-33071 Oviedo, Spain

Rodríguez, F
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机构: Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada, CSIC, E-33071 Oviedo, Spain

Vadecard, J
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机构: Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada, CSIC, E-33071 Oviedo, Spain

Bendix, M
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机构: Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada, CSIC, E-33071 Oviedo, Spain

Fañanás, FJ
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机构: Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada, CSIC, E-33071 Oviedo, Spain

López-Ortiz, F
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机构: Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada, CSIC, E-33071 Oviedo, Spain

Rodríguez, MA
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机构: Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada, CSIC, E-33071 Oviedo, Spain
机构:
[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada, CSIC, E-33071 Oviedo, Spain
[2] Univ Almeria, Dept Geometria Topol & Quim Organ, Fac Ciencias Expt, E-04120 Almeria, Spain
[3] Univ La Rioja, Dept Quim, E-26071 Logrono, Spain
关键词:
D O I:
10.1021/ja991161+
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
In-situ-generated dialkylboroxy and diaminoboroxy Fischer carbene complexes lead to oxaborolane or oxazaborolidine derivatives via an intramolecular C-II insertion reaction. Further oxidation of these intermediates yields 1,3-diol or 1,2-amino alcohol derivatives. Diastereoselectivities as high as 99% are reached when starting from boroxy Fischer carbene complexes derived from terpenes, which represents a regio- and diastereoselective modification of this type of natural product. The influence of the C-beta substituents relative to the boron atom on the reaction path is studied, and a mechanism is proposed after identification of an intermediate by NMR. In addition, theoretical calculations show the presence of a boron-metal interaction, which could result as key step to the C-H insertion reaction.
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页码:8776 / 8782
页数:7
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共 66 条
- [1] TRISAMINOBORANES[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1962, (10): : 4088 - &AUBREY, DW论文数: 0 引用数: 0 h-index: 0MAJUMDAR, MK论文数: 0 引用数: 0 h-index: 0LAPPERT, MF论文数: 0 引用数: 0 h-index: 0
- [2] INTRAMOLECULAR BENZANNULATION REACTIONS OF MANGANESE CARBENE COMPLEXES[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (22) : 8735 - 8736BALZER, BL论文数: 0 引用数: 0 h-index: 0机构: UNIV VIRGINIA,DEPT CHEM,CHARLOTTESVILLE,VA 22901 UNIV VIRGINIA,DEPT CHEM,CHARLOTTESVILLE,VA 22901CAZANOUE, M论文数: 0 引用数: 0 h-index: 0机构: UNIV VIRGINIA,DEPT CHEM,CHARLOTTESVILLE,VA 22901 UNIV VIRGINIA,DEPT CHEM,CHARLOTTESVILLE,VA 22901FINN, MG论文数: 0 引用数: 0 h-index: 0机构: UNIV VIRGINIA,DEPT CHEM,CHARLOTTESVILLE,VA 22901 UNIV VIRGINIA,DEPT CHEM,CHARLOTTESVILLE,VA 22901
- [3] THE 1ST BENZANNULATION CHEMISTRY OF MANGANESE CARBENE COMPLEXES - ACTIVATION BY D(0) METALATION[J]. ORGANOMETALLICS, 1992, 11 (05) : 1759 - 1761BALZER, BL论文数: 0 引用数: 0 h-index: 0机构: UNIV VIRGINIA, DEPT CHEM, CHARLOTTESVILLE, VA 22901 USA UNIV VIRGINIA, DEPT CHEM, CHARLOTTESVILLE, VA 22901 USACAZANOUE, M论文数: 0 引用数: 0 h-index: 0机构: UNIV VIRGINIA, DEPT CHEM, CHARLOTTESVILLE, VA 22901 USA UNIV VIRGINIA, DEPT CHEM, CHARLOTTESVILLE, VA 22901 USASABAT, M论文数: 0 引用数: 0 h-index: 0机构: UNIV VIRGINIA, DEPT CHEM, CHARLOTTESVILLE, VA 22901 USA UNIV VIRGINIA, DEPT CHEM, CHARLOTTESVILLE, VA 22901 USAFINN, MG论文数: 0 引用数: 0 h-index: 0机构: UNIV VIRGINIA, DEPT CHEM, CHARLOTTESVILLE, VA 22901 USA UNIV VIRGINIA, DEPT CHEM, CHARLOTTESVILLE, VA 22901 USA
- [4] Alkenyl Fischer carbene complexes and alpha,beta-unsaturated imine derivatives: Synthesis of azepines and mechanistic NMR studies[J]. CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (01) : 88 - 97Barluenga, J论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAINTomas, M论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAINBallesteros, A论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAINSantamaria, J论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAINCarbajo, RJ论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAINLopezOrtiz, F论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAINGarciaGranda, S论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN论文数: 引用数: h-index:机构:
- [5] Difluoroboroxymolybdenum Fischer carbene complexes as precursors of acyl radicals: Dimerization and trapping with 3-buten-2-one[J]. ORGANOMETALLICS, 1997, 16 (25) : 5384 - 5385Barluenga, J论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al CSIC, Universidad de Oviedo, E-33071 Oviedo, Julián ClaveríaRodriguez, F论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al CSIC, Universidad de Oviedo, E-33071 Oviedo, Julián ClaveríaFananas, FJ论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al CSIC, Universidad de Oviedo, E-33071 Oviedo, Julián Clavería
- [6] Cyclic BF2 adducts of functionalized fischer vinylcarbene complexes:: Preparation and stereoselective Diels-Alder reactions with 2-amino 1,3-dienes[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) : 2514 - 2522Barluenga, J论文数: 0 引用数: 0 h-index: 0机构: Inst Univ Quim Organomet Enrique Moles, Unidad Asoc CSIC, Oviedo, Spain Inst Univ Quim Organomet Enrique Moles, Unidad Asoc CSIC, Oviedo, SpainCanteli, RM论文数: 0 引用数: 0 h-index: 0机构: Inst Univ Quim Organomet Enrique Moles, Unidad Asoc CSIC, Oviedo, SpainFlorez, J论文数: 0 引用数: 0 h-index: 0机构: Inst Univ Quim Organomet Enrique Moles, Unidad Asoc CSIC, Oviedo, SpainGarcia-Granda, S论文数: 0 引用数: 0 h-index: 0机构: Inst Univ Quim Organomet Enrique Moles, Unidad Asoc CSIC, Oviedo, SpainGutierrez-Rodriguez, A论文数: 0 引用数: 0 h-index: 0机构: Inst Univ Quim Organomet Enrique Moles, Unidad Asoc CSIC, Oviedo, SpainMartin, E论文数: 0 引用数: 0 h-index: 0机构: Inst Univ Quim Organomet Enrique Moles, Unidad Asoc CSIC, Oviedo, Spain
- [7] ASYMMETRIC EXO-SELECTIVE DIELS-ALDER REACTIONS OF CYCLIC BF2 ADDUCTS OF FUNCTIONALIZED FISCHER VINYLCARBENE COMPLEXES WITH CHIRAL 2-AMINO-1,3-DIENES[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) : 6949 - 6950BARLUENGA, J论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAINCANTELI, RM论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAINFLOREZ, J论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAINGARCIAGRANDA, S论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAINGUTIERREZRODRIGUEZ, A论文数: 0 引用数: 0 h-index: 0机构: UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN
- [8] Formal [4+3], [4+2], [4+1] and [2+1] cycloadditions and acid-base reaction of 2-methyl-1,3-dimorpholino-1,3-butadiene with Fischer carbene complexes[J]. CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (10) : 1629 - 1637Barluenga, J论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al C. S. I. C., E-33071 Oviedo, Julián Clavería s/nAznar, F论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al C. S. I. C., E-33071 Oviedo, Julián Clavería s/nFernandez, M论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al C. S. I. C., E-33071 Oviedo, Julián Clavería s/n
- [9] Intramolecular C-H insertion reactions of boroxy Fischer carbene complexes[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (25) : 6090 - 6091Barluenga, J论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al CSIC, Universidad de Oviedo, E-33071 Oviedo, Julián ClaveríaRodriguez, F论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al CSIC, Universidad de Oviedo, E-33071 Oviedo, Julián ClaveríaVadecard, J论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al CSIC, Universidad de Oviedo, E-33071 Oviedo, Julián ClaveríaBendix, M论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al CSIC, Universidad de Oviedo, E-33071 Oviedo, Julián ClaveríaFananas, FJ论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al CSIC, Universidad de Oviedo, E-33071 Oviedo, Julián ClaveríaLopezOrtiz, F论文数: 0 引用数: 0 h-index: 0机构: Inst. Univ. Quim. Orgmet. Enrique M., Unidad Asociada al CSIC, Universidad de Oviedo, E-33071 Oviedo, Julián Clavería
- [10] H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) : 2093 - 2094BAX, A论文数: 0 引用数: 0 h-index: 0机构: US FDA,DIV BIOCHEM,BIOPHYS LAB,BETHESDA,MD 20892 US FDA,DIV BIOCHEM,BIOPHYS LAB,BETHESDA,MD 20892SUMMERS, MF论文数: 0 引用数: 0 h-index: 0机构: US FDA,DIV BIOCHEM,BIOPHYS LAB,BETHESDA,MD 20892 US FDA,DIV BIOCHEM,BIOPHYS LAB,BETHESDA,MD 20892