Palladium catalysed tandem cyclisation-anion capture. Part 8: Cascade hydrostannylation-cyclisation-anion capture and cascade hydroboration-cyclisation-anion capture on solid phase

被引:14
作者
Grigg, R [1 ]
MacLachlan, WS
MacPherson, DT
Sridharan, V
Suganthan, S
机构
[1] Univ Leeds, Sch Chem, Mol Innovat Divers & Automated Synth Ctr MIDAS, Leeds LS2 9JT, W Yorkshire, England
[2] GlaxoSmithKline, Harlow CM19 5AW, Essex, England
关键词
cascade reactions; palladium catalysis; hydrostannylation; hydroboration; Stille coupling; Suzuki coupling; cyclisation;
D O I
10.1016/S0040-4020(01)01061-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Up to four bonds and five stereocentres are created, in five component processes (five point diversity), utilising resin bound aryl iodides by hydroboration or hydrostannylation of alkynes, followed by cyclisation-anion capture involving Suzuki or Stille reactions. Three small libraries were prepared to validate the chemistry. (C) 2001 Elsevier Science Ltd. All fights reserved.
引用
收藏
页码:10335 / 10345
页数:11
相关论文
共 21 条
  • [1] Palladium catalysed queuing processes. Part 2: Termolecular cyclization-anion capture employing carbon monoxide as a relay switch with in situ generated vinylstannanes
    Anwar, U
    Casaschi, A
    Grigg, R
    Sansano, JM
    [J]. TETRAHEDRON, 2001, 57 (07) : 1361 - 1367
  • [2] BARRA ED, 1994, HETEROCYCLES, V38, P1367
  • [3] BROWN HC, 1975, J AM CHEM SOC, V97, P5225
  • [4] Palladium catalysed queuing processes. Part 1: Termolecular cyclization-anion capture employing carbon monoxide as a relay switch and hydride, organotin(IV) or boron reagents
    Brown, S
    Clarkson, S
    Grigg, R
    Thomas, WA
    Sridharan, V
    Wilson, DM
    [J]. TETRAHEDRON, 2001, 57 (07) : 1347 - 1359
  • [5] THE ANOMALOUS STILLE REACTIONS OF METHYL ALPHA-(TRIBUTYLSTANNYL)ACRYLATE - EVIDENCE FOR A PALLADIUM CARBENE INTERMEDIATE
    BUSACCA, CA
    SWESTOCK, J
    JOHNSON, RE
    BAILEY, TR
    MUSZA, L
    RODGER, CA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) : 7553 - 7556
  • [6] TIN RADICAL-ADDITION TO ALKYNYL SULFIDES - REACTIVITY OF THE INTERMEDIATE THIOALKYL-SUBSTITUTED BETA-(TRIBUTYLSTANNYL)VINYL RADICALS
    CAPELLA, L
    MONTEVECCHI, PC
    NANNI, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) : 3368 - 3374
  • [7] Palladium catalysed tandem cyclisation-anion capture. Part 5: Cascade hydrostannylation-bis-cyclisation-intramolecular anion capture. Synthesis of bridged- and spiro-cyclic small and macrocyclic heterocycles
    Casaschi, A
    Grigg, R
    Sansano, JM
    Wilson, D
    Redpath, J
    [J]. TETRAHEDRON, 2000, 56 (38) : 7541 - 7551
  • [8] Palladium catalysed tandem cyclisation-anion capture.: Part 6:: Synthesis of sugar, nucleoside, purine, benzodiazepinone and β-lactam analogues via capture of in situ generated vinylstannanes
    Casaschi, A
    Grigg, R
    Sansano, JM
    [J]. TETRAHEDRON, 2000, 56 (38) : 7553 - 7560
  • [9] CASASCHI A, 2000, TETRAHEDRON, V56, P7525
  • [10] COPPOLA RA, 1993, SYNTHETIC COMMUN, P2003