The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups

被引:408
作者
Trost, Barry M. [1 ]
Weiss, Andrew H. [2 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
[2] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
alkynylation; catalytic asymmetric synthesis; propargylic alcohols; propargylic amines; CATALYTIC ASYMMETRIC ADDITION; IN-SITU GENERATION; PONNDORF-VERLEY ALKYNYLATION; CONJUGATE ADDITION; TERMINAL ALKYNES; PROPARGYLIC ALCOHOLS; AROMATIC-ALDEHYDES; GAMMA-HYDROXY-ALPHA; BETA-ACETYLENIC ESTERS; ALKYNYLZINC REAGENTS; PHENYLACETYLENE ADDITIONS;
D O I
10.1002/adsc.200800776
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Over the past decade, large strides have been achieved in the invention of methods for the direct enantioselective addition of alkynes and metal alkynylide nucleophiles into prochiral aldehydes, ketones, and imines. This review highlights and compares the available methods for these transformations.
引用
收藏
页码:963 / 983
页数:21
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共 178 条
[1]   Total synthesis of FR901464, an antitumor agent that regulates the transcription of oncogenes and tumor suppressor genes [J].
Albert, BJ ;
Sivaramakrishnan, A ;
Naka, T ;
Koide, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) :2792-2793
[2]   Stereoselective approach to alk-2-yne-1,4-diols. Application to the synthesis of musclide B [J].
Amador, M ;
Ariza, X ;
Garcia, J ;
Ortiz, J .
TETRAHEDRON LETTERS, 2002, 43 (15) :2691-2694
[3]   A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].
Anand, NK ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688
[4]   Enantioselective addition of phenyl and alkyl acetylenes to imines catalyzed by chiral Cu(I) complexes [J].
Benaglia, M ;
Negri, D ;
Dell'Anna, G .
TETRAHEDRON LETTERS, 2004, 45 (47) :8705-8708
[5]   Enantioselective one-pot three-component synthesis of propargylamines [J].
Bisai, Alakesh ;
Singh, Vinod K. .
ORGANIC LETTERS, 2006, 8 (11) :2405-2408
[6]   Highly enantioselective zinc/binol-catalyzed alkynylation of N-sulfonyl aldimines [J].
Blay, Gonzalo ;
Cardona, Luz ;
Climent, Estela ;
Pedro, Jose R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (30) :5593-5596
[7]   Stereoselective syntheses of epothilones A and B via directed nitrile oxide cycloaddition [J].
Bode, JW ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) :3611-3612
[8]   Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes [J].
Boyall, D ;
López, F ;
Sasaki, H ;
Frantz, D ;
Carreira, EM .
ORGANIC LETTERS, 2000, 2 (26) :4233-4236
[9]   SYNTHESIS OF CHIRAL ALK-1-YNES CONTAINING AN ALPHA-PHENYLETHYL GROUP [J].
CAPORUSSO, AM ;
LARDICCI, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (05) :949-953
[10]   Advances in indium-catalysed organic synthesis [J].
Chauhan, KK ;
Frost, CG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (18) :3015-3019