Functionalized bicyclo[3.3.0]octanes by enantioselective transannular desymmetrization

被引:30
作者
Hodgson, DM [1 ]
Cameron, ID [1 ]
机构
[1] Univ Oxford, Dept Chem, Dyson Perrins Lab, Oxford OX1 3QY, England
关键词
D O I
10.1021/ol006947n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Enantioselective alpha -deprotonation-rearrangement of achiral substituted cyclooctene oxides 7, 17, and 18 using organolithiums in the presence of (-)-sparteine (3) or (-)-alpha -isosparteine (4) gives the functionalized bicyclo[3.3.0]octen-2 ols 8, 19, and 20 in 56-72% yields and 83-89% ee's.
引用
收藏
页码:441 / 444
页数:4
相关论文
共 34 条
  • [1] SIMPLE DESIGNS FOR THE CONSTRUCTION OF COMPLEX TRANS-FUSED POLYETHER TOXIN FRAMEWORKS - A LINEAR STRATEGY BASED ON ENTROPICALLY FAVORED OXIRANE RING ENLARGEMENT IN EPOXYCYCLOALKENES FOLLOWED BY CARBON-CARBON OR CARBON-OXYGEN BOND-FORMING CYCLIZATIONS
    ALVAREZ, E
    DIAZ, MT
    PEREZ, R
    RAVELO, JL
    REGUEIRO, A
    VERA, JA
    ZURITA, D
    MARTIN, JD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) : 2848 - 2876
  • [2] Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications
    Beak, P
    Basu, A
    Gallagher, DJ
    Park, YS
    Thayumanavan, S
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) : 552 - 560
  • [3] BOECKMAN RK, 1977, TETRAHEDRON LETT, P4281
  • [4] TRANSANNULAR REACTIONS IN MEDIUM-SIZED RINGS
    COPE, AC
    MARTIN, MM
    MCKERVEY, MA
    [J]. QUARTERLY REVIEWS, 1966, 20 (01): : 119 - &
  • [5] CIS,CIS-1,5-CYCLOOCTADIENE DIEPOXIDE
    COPE, AC
    FISHER, BS
    FUNKE, W
    MCINTOSH, JM
    MCKERVEY, MA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (07) : 2231 - &
  • [6] PROXIMITY EFFECTS .12. REACTION OF CIS-CYCLOOCTENE AND TRANS-CYCLOOCTENE OXIDE WITH BASES
    COPE, AC
    LEE, HH
    PETREE, HE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (11) : 2849 - 2852
  • [7] CRANDALL JK, 1983, ORG REACTIONS, V29, P345
  • [8] A NEW METHOD FOR THE DEOXYGENATION OF TERTIARY AND SECONDARY ALCOHOLS
    DOLAN, SC
    MACMILLAN, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (22) : 1588 - 1589
  • [9] Asymmetric rearrangement of N-Boc 7-azanorbornene oxide:: use of aryllithiums for enantioselective deprotonation
    Hodgson, DM
    Maxwell, CR
    Matthews, IR
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (10) : 1847 - 1850
  • [10] Enantioselective alpha-deprotonation-rearrangement of meso-epoxides
    Hodgson, DM
    Lee, GP
    [J]. CHEMICAL COMMUNICATIONS, 1996, (09) : 1015 - 1016