Atroposelectivity in the reactions of ortholithiated aromatic tertiary amides with aldehydes

被引:84
作者
Bowles, P [1 ]
Clayden, J [1 ]
Helliwell, M [1 ]
McCarthy, C [1 ]
Tomkinson, M [1 ]
Westlund, N [1 ]
机构
[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCS,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 17期
关键词
D O I
10.1039/a701671i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The products of the addition of ortholithiated N,N-dialkylnaphthamides to aldehydes are pairs of stable,diastereoisomeric atropisomers, formed with selectivities of up to 90:10 in favour bf the syn-atropisomer.
引用
收藏
页码:2607 / 2616
页数:10
相关论文
共 69 条
  • [1] ACKERMAN JH, 1969, TETRAHEDRON LETT, P4487
  • [2] ACKERMAN JH, 1969, TETRAHEDRON LETT, P3879
  • [3] ENANTIOSELECTIVE ORTHO-LITHIATION OF BENZALDEHYDE CHROMIUMTRICARBONYL COMPLEX
    ALEXAKIS, A
    KANGER, T
    MANGENEY, P
    ROSEMUNCH, F
    PERROTEY, A
    ROSE, E
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (09) : 2135 - 2138
  • [4] ENANTIOSELECTIVE ORTHO-LITHIATION OF AMINALS OF BENZALDEHYDE CHROMIUMTRICARBONYL COMPLEX
    ALEXAKIS, A
    KANGER, T
    MANGENEY, P
    ROSEMUNCH, F
    PERROTEY, A
    ROSE, E
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (01) : 47 - 50
  • [5] NEW ORGANIC COMPOUNDS FOR USE IN INSECT CONTROL
    ALEXANDER, BH
    GERTLER, SI
    ODA, TA
    BROWN, RT
    IHNDRIS, RW
    BEROZA, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (04) : 626 - 632
  • [6] ENANTIOFACE-DIFFERENTIATING ADDITION OF A CHIRAL ARYLLITHIUM REAGENT TO ALDEHYDES
    ASAMI, M
    MUKAIYAMA, T
    [J]. CHEMISTRY LETTERS, 1980, (01) : 17 - 20
  • [7] ASYMMETRIC DEPROTONATION AND COMPLEXATION REACTIONS MEDIATED BY CHIRAL KETALS AS A ROUTE TO ORTHO-DISUBSTITUTED (ETA-6-ARENE)CR(CO)3 COMPLEXES
    AUBE, J
    HEPPERT, JA
    MILLIGAN, ML
    SMITH, MJ
    ZENK, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) : 3563 - 3570
  • [8] SYNTHESIS OF THE C-GLYCOSIDE FRAGMENT OF NOGALAMYCIN AND SOME NOGALAMYCIN PRECURSORS
    BATES, MA
    SAMMES, PG
    THOMSON, GA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (11): : 3037 - 3045
  • [9] MONOMERIC ORGANOLITHIUM COMPOUNDS IN TETRAHYDROFURAN - TERT-BUTYLLITHIUM, SEC-BUTYLLITHIUM, SUPERMESITYLLITHIUM, MESITYLLITHIUM, AND PHENYLLITHIUM - CARBON LITHIUM COUPLING-CONSTANTS AND THE NATURE OF CARBON LITHIUM BONDING
    BAUER, W
    WINCHESTER, WR
    SCHLEYER, PV
    [J]. ORGANOMETALLICS, 1987, 6 (11) : 2371 - 2379
  • [10] DEGREE OF AGGREGATION OF ORGANO-LITHIUM COMPOUNDS BY MEANS OF CRYOSCOPY IN TETRAHYDROFURAN
    BAUER, W
    SEEBACH, D
    [J]. HELVETICA CHIMICA ACTA, 1984, 67 (07) : 1972 - 1988