Catalyzed Propargylic Substitution

被引:237
作者
Detz, Remko J. [1 ]
Hiemstra, Henk [1 ]
van Maarseveen, Jan H. [1 ]
机构
[1] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1018 WS Amsterdam, Netherlands
关键词
Alkynes; Copper; Enantioselectivity; Ruthenium; ONE-POT SYNTHESIS; PROPARGYLATION/CYCLOISOMERIZATION TANDEM REACTION; BRIDGED DIRUTHENIUM COMPLEXES; BOND-FORMING REACTIONS; NUCLEOPHILIC-SUBSTITUTION; 1,3-DICARBONYL COMPOUNDS; CENTERED NUCLEOPHILES; RUTHENIUM CATALYSTS; ALLYLIC ALKYLATIONS; AROMATIC-COMPOUNDS;
D O I
10.1002/ejoc.200900877
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Besides being a versatile entity for further chemical transformations, the propargylic subunit is also part of various natural products, fine chemicals, and synthetic pharmaceuticals. Propargylic substitution reactions, however, are rather unexplored. An overview of this emerging field is presented. We especially focus on experimental results that deal with catalyzed substitutions of propargylic alcohols and their derivatives. Finally, some enantioselective propargylic substitution methods are discussed. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码:6263 / 6276
页数:14
相关论文
共 100 条
[1]  
[Anonymous], TETRAHEDRON LETT
[2]   Sequential gold-catalyzed reactions of 1-phenylprop-2-yn-1-ol with 1,3-dicarbonyl compounds [J].
Arcadi, Antonio ;
Alfonsi, Maria ;
Chiarini, Marco ;
Marinelli, Fabio .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) :576-582
[3]   π-Activated alcohols: an emerging class of alkylating agents for catalytic Friedel-Crafts reactions [J].
Bandini, Marco ;
Tragni, Michele .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (08) :1501-1507
[4]   Synthesis of propargylic ethers via Lewis-acid mediated nucleophilic substitution of propargylic esters [J].
Bartels, A ;
Mahrwald, R ;
Quint, S .
TETRAHEDRON LETTERS, 1999, 40 (33) :5989-5990
[5]  
BELL D, 1995, SYNTHESIS-STUTTGART, P707
[6]   DIRECT DISPLACEMENT AND COUPLING OF PROP-2-YNYLIC ACETATES WITH ORGANOCUPRATES [J].
BRINKMEYER, RS ;
MACDONALD, TL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (20) :876-877
[7]   Mononuclear ruthenium catalysts for the direct propargylation of heterocycles with propargyl alcohols [J].
Bustelo, E ;
Dixneuf, PH .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :393-397
[8]   One-pot three-component catalytic synthesis of fully substituted pyrroles from readily available propargylic alcohols, 1,3-dicarbonyl compounds and primary amines [J].
Cadierno, Victorio ;
Gimeno, Jose ;
Nebra, Noel .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (35) :9973-9981
[9]   A novel propargylation/cycloisomerization tandem process catalyzed by a ruthenium(II)/trifluoroacetic acid system: One-pot entry to fully substituted furans from readily available secondary propargylic alcohols and 1,3-dicarbonyl compounds [J].
Cadierno, Victorio ;
Gimeno, Jose ;
Nebra, Noel .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) :382-394
[10]   STEREOSELECTIVE PROPARGYLATION MEDIATED BY A CHIRAL METAL CLUSTER - REACTIONS OF [(PROPARGYLIUM)CO2(CO)5-(P(OR)3)][BF4] WITH CARBON NUCLEOPHILES [J].
CAFFYN, AJM ;
NICHOLAS, KM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6438-6439