Catalytic Asymmetric Conjugate Addition of α-Cyanoketones for the Construction of a Quaternary Stereogenic Center

被引：35
作者：
Kawato, Yuji [1 ]
Takahashi, Noriko [1 ]
Kumagai, Naoya [1 ]
Shibasaki, Masakatsu [1 ]
机构：
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 07期
关键词：
DIELS-ALDER REACTIONS; ENANTIOSELECTIVE CONSTRUCTION; MICHAEL ADDITIONS; ALPHA; BETA-UNSATURATED KETONES; 1,3-DICARBONYL COMPOUNDS; SYNTHETIC ENZYMES; ALDOL REACTIONS; STEREOCENTERS; EPOXIDATION; CYANOACETATES;
D O I：
10.1021/ol100183s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The catalytic asymmetric conjugate addition of alpha-cyanoketone pronucleophiles to vinyl ketones promoted by a Y/1 catalyst is described. High enantioselectivity was observed for a range of aromatic vinyl ketones, providing 1,5-dicarbonyl compounds bearing an all-carbon quaternary stereogenic center. The product was successfully converted to a spiro-piperidine entity and a bicyclo[3.3.0]octane framework through either the reduction of nitrile or intramolecular pinacol coupling.
引用
收藏
页码：1484 / 1487
页数：4
相关论文
共 66 条
  • [1] Organocatalytic asymmetric "anti-Michael" reaction of β-ketoesters
    Aleman, Jose
    Reyes, Efraim
    Richter, Bo
    Overgaard, Jacob
    Jorgensen, Karl Anker
    [J]. CHEMICAL COMMUNICATIONS, 2007, (38) : 3921 - 3923
  • [2] Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
  • [3] Arseniyadis S., 1984, Org. React, V31, P1, DOI DOI 10.1002/0471264180.OR031.01
  • [4] Organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides
    Bartoli, Giuseppe
    Bosco, Marcella
    Carlone, Armando
    Cavalli, Andrea
    Locatelli, Manuela
    Mazzanti, Andrea
    Ricci, Paolo
    Sambri, Letizia
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) : 4966 - 4970
  • [5] Organocatalytic enantioselective nucleophilic vinylic substitution by α-substituted-α-cyanoacetates under phase-transfer conditions
    Bell, Mark
    Poulsen, Thomas B.
    Jorgensen, Karl Anker
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08) : 3053 - 3056
  • [6] Studies of folded peptide-based catalysts for asymmetric organic synthesis
    Blank, JT
    Miller, SJ
    [J]. BIOPOLYMERS, 2006, 84 (01) : 38 - 47
  • [7] Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of β-ketoesters
    Capuzzi, Marinella
    Perdicchia, Dario
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (01) : 128 - 135
  • [8] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions
    Christoffers, J
    Baro, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) : 1688 - 1690
  • [9] Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
  • [10] 2-V
1234567