Intramolecular Diels-Alder reactions. 5 - Facile synthesis of an octahydrobenzocycloheptenone derivative utilising intramolecular Diels-Alder reaction

被引：0
|
作者：
Frey, B [1 ]
Reissig, HU [1 ]
机构：
[1] Tech Univ Dresden, Inst Organ Chem, D-01062 Dresden, Germany
来源：
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1999年 / 341卷 / 02期
关键词：
carbocycles; cycloadditions; Lewis acids; titanium; cycloheptanone;
D O I：
10.1002/(SICI)1521-3897(199902)341:2<173::AID-PRAC173>3.0.CO;2-M
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Undecatrienone 4 was prepared in a short sequence via siloxycyclopropanes 1 and 3. Intramolecular Diels-Alder reaction (IMDA) of 4 under various conditions afforded octahydrobenzocycloheptenone derivative 5 as a mixture of three or four diastereomers. High diastereoselectivities in favour of the endo-product cis-5a could be obtained with TiCl4 as promoter. This selectivities were attributed to the formation of a seven-membered ring chelate as intermediate. The configurational assignment of all four diastereomers of 5 was based on isomerisation reactions and NMR analysis.
引用
收藏
页码：173 / 178
页数：6
相关论文
共 50 条
  • [21] INTRAMOLECULAR DIELS-ALDER REACTIONS OF THE FURAN DIENE
    STERNBACH, DD
    ROSSANA, DM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1982, 183 (MAR): : 130 - ORGN
  • [22] RATES OF INTRAMOLECULAR DIELS-ALDER REACTIONS OF PENTADIENYLACRYLAMIDES
    GSCHWEND, HW
    LEE, AO
    MEIER, HP
    JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (12): : 2169 - 2175
  • [23] The first intramolecular silene Diels-Alder reactions
    Czyzewski, Michal
    Sellars, Jonathan D.
    Guliashvili, Tamaz
    Tibbelin, Julius
    Johnstone, Lisa
    Bower, Justin
    Box, Matthew
    Davies, Robert D. M.
    Ottosson, Henrik
    Steel, Patrick G.
    CHEMICAL COMMUNICATIONS, 2014, 50 (22) : 2919 - 2921
  • [24] Alkenylboronate tethered intramolecular Diels-Alder reactions
    Batey, RA
    Thadani, AN
    Lough, AJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) : 450 - 451
  • [25] INTRAMOLECULAR DIELS-ALDER REACTIONS IN ARYL ALLENECARBOXYLATES
    HIMBERT, G
    FINK, D
    TETRAHEDRON LETTERS, 1985, 26 (36) : 4363 - 4366
  • [26] INTRAMOLECULAR DIELS-ALDER REACTION OF IMINOTHIOL ESTERS
    TAMARU, Y
    ISHIGE, O
    KAWAMURA, S
    YOSHIDA, Z
    TETRAHEDRON LETTERS, 1984, 25 (33) : 3583 - 3586
  • [27] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION
    CRAIG, D
    CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) : 187 - 238
  • [28] A TANDEM OXIDATION INTRAMOLECULAR DIELS-ALDER REACTION
    WU, HJ
    KAI, P
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (12) : 898 - 900
  • [29] Allylic stereocontrol of the intramolecular Diels-Alder reaction
    Lilly, MJ
    Miller, NA
    Edwards, AJ
    Willis, AC
    Turner, P
    Paddon-Row, MN
    Sherburn, MS
    CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) : 2525 - 2536
  • [30] Complexation control of pericyclic reactions. Supramolecular effects on the intramolecular diels-alder reaction
    1600, (113):
12345