Sequential hydrostannylation-cyclisation of delta- and omega-allenyl aryl halides. Cyclisation at the proximal carbon.

被引：33
作者：
Grigg, R
Sansano, JM
机构：
[1] School of Chemistry, Leeds University
来源：
TETRAHEDRON | 1996年 / 52卷 / 42期
关键词：
D O I：
10.1016/0040-4020(96)00801-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium catalysed hydrostannylation of (Bu(3)SnH, THF, degrees C) of delta- and omega-allenyl aryl halides followed by mono- or bis-cyclisation (MeCN, 80 degrees C) affords small (5-7), large (11-17) and spirocyclic rings in which cyclisation occurs at the proximal carbon of the original allene. The reaction proceeds via stereoselective allylstannane formation. The cyclisation products are alpha-vinyl oxygen- and nitrogen-heterocycles. Copyright (C) 1996 Elsevier Science Ltd
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页码：13441 / 13454
页数：14
相关论文
共 31 条
[1]  
AMES C, 1996, J CHEM RES, P116
[2]   TOTAL SYNTHESIS OF THE TRIQUINANE MARINE SESQUITERPENE (PLUS-OR-MINUS)DELTA(9(12)) CAPNELLENE USING A PALLADIUM-CATALYZED BIS-CYCLIZATION STEP [J].
BALME, G ;
BOUYSSI, D .
TETRAHEDRON, 1994, 50 (02) :403-414
[3]   PALLADIUM-CATALYZED ALKYLATIVE CYCLIZATION OF 2,3-BUTADIANYLMALONATES TO GAMMA-LACTONES [J].
BESSON, L ;
BAZIN, J ;
GORE, J ;
CAZES, B .
TETRAHEDRON LETTERS, 1994, 35 (18) :2881-2884
[4]   PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES [J].
BURNS, B ;
GRIGG, R ;
SANTHAKUMAR, V ;
SRIDHARAN, V ;
STEVENSON, P ;
WORAKUN, T .
TETRAHEDRON, 1992, 48 (35) :7297-7320
[5]   Palladium catalysed cascade hydrostannylation-bis-cyclisation-intramolecular anion capture, routes to bridged- and spiro-cyclic small and macrocyclic heterocycles. [J].
Casaschi, A ;
Grigg, R ;
Sansano, JM ;
Wilson, D ;
Redpath, J .
TETRAHEDRON LETTERS, 1996, 37 (25) :4413-4416
[6]   SYNTHETIC METHODOLOGY INVOLVING THE CARBOPALLADATION OF ALLENES [J].
CAZES, B .
PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1867-1878
[7]   CARBOPALLADATION OF FUNCTIONALIZED ALLENES - REGIOSELECTIVITY OF THE REACTION OF CARBONUCLEOPHILES WITH THE INTERMEDIATE PI-ALLYL PALLADIUM COMPLEXES [J].
CHAPTAL, N ;
COLOVRAYGOTTELAND, V ;
GRANDJEAN, C ;
CAZES, B ;
GORE, J .
TETRAHEDRON LETTERS, 1991, 32 (15) :1795-1798
[8]   Palladium heteroannulation process for synthesis of substituted pyrrolo [2,3-b]pyridin-3-ones [J].
Desarbre, E ;
Merour, JY .
TETRAHEDRON LETTERS, 1996, 37 (01) :43-46
[9]   Novel Pd(0)-catalyzed intramolecular reactions of allylic acetates with allenic moieties followed by tandem cyclization [J].
Doi, T ;
Yanagisawa, A ;
Nakanishi, S ;
Yamamoto, K ;
Takahashi, T .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2602-2603
[10]   PALLADIUM-CATALYZED CASCADE CARBONYLATION-CYCLIZATION-CARBOMETALLATION-ANION CAPTURE - TETRAMOLECULAR QUEUING-PROCESSES [J].
GRIGG, R ;
REDPATH, J ;
SRIDHARAN, V ;
WILSON, D .
TETRAHEDRON LETTERS, 1994, 35 (41) :7661-7664
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