Highly enantioselective hetero-Diels-Alder reactions between Rawal's diene and aldehydes catalyzed by chiral dirhodium(II) carboxamidates

被引：20
|
作者：
Watanabe, Yudai [1 ]
Washio, Takuya [1 ]
Shimada, Naoyuki [1 ]
Anada, Masahiro [1 ]
Hashimoto, Shunichi [1 ]
机构：
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 060, Japan
来源：
CHEMICAL COMMUNICATIONS | 2009年 / 47期
关键词：
ONE-STEP SYNTHESIS; HYDROGEN-BOND; ASYMMETRIC SYNTHESES; ALIPHATIC-ALDEHYDES; DANISHEFSKYS DIENE; BRASSARD DIENE; REACTIVITY; ROUTE; 1-AMINO-3-SILOXY-1,3-BUTADIENES; INTERACTIVITY;
D O I：
10.1039/b919535a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first example of a chiral Lewis acid-catalyzed enantioselective hetero-Diels-Alder (HDA) reaction between 1-dimethylamino-3-silyloxy-1,3-butadiene (Rawal's diene) and aldehydes is described. The cycloaddition reaction under the influence of 1 mol% of dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh-2(S-BPTPI)(4), proceeded cleanly and gave, after treatment with acetyl chloride, the corresponding dihydropyranones in up to 99% ee.
引用
收藏
页码：7294 / 7296
页数：3
相关论文
共 50 条
  • [1] Influence of the diene in the Hetero-Diels-Alder reaction catalyzed by dirhodium(II) carboxamidates
    Valenzuela, M
    Doyle, MP
    Hedberg, C
    Hu, WH
    Holmstrom, A
    [J]. SYNLETT, 2004, (13) : 2425 - 2428
  • [2] Chiral dirhodium(II) carboxamidates as Lewis acids for hetero-Diels-Alder reactions
    Valenzuela, MV
    Doyle, MP
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U317 - U317
  • [3] Asymmetric hetero-Diels-Alder reaction catalyzed by dirhodium(II) carboxamidates
    Doyle, MP
    Valenzuela, M
    Huang, PL
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5391 - 5395
  • [4] Enantio- and diastereoselective hetero-Diels-Alder reactions between 4-methyl-substituted Rawal's diene and aldehydes catalyzed by chiral dirhodium(II) carboxamidates: catalytic asymmetric synthesis of (-)-cis-aerangis lactone
    Watanabe, Yudai
    Shimada, Naoyuki
    Anada, Masahiro
    Hashimoto, Shunichi
    [J]. TETRAHEDRON-ASYMMETRY, 2014, 25 (01) : 63 - 73
  • [5] Asymmetric Hetero-Diels-Alder Reactions Catalyzed by Chiral Dirhodium (II) Complexes
    Anada, Masahiro
    Hashimoto, Shunichi
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2019, 77 (06) : 553 - 565
  • [6] Highly enantioselective hetero-Diels-Alder reaction of brassard diene with aromatic aldehydes
    Fan, Q
    Lin, LL
    Liu, J
    Huang, YZ
    Feng, XM
    Zhang, GL
    [J]. ORGANIC LETTERS, 2004, 6 (13) : 2185 - 2188
  • [7] A new class of chiral Lewis acid catalysts for highly enantioselective hetero-Diels-Alder reactions: Exceptionally high turnover numbers from dirhodium(II) carboxamidates
    Doyle, MP
    Phillips, IM
    Hu, WH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) : 5366 - 5367
  • [8] Enantio- and diastereoselective hetero-Diels-Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(II) carboxamidates
    Watanabe, Yudai
    Washio, Takuya
    Krishnamurthi, Janagiraman
    Anada, Masahiro
    Hashimoto, Shunichi
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (55) : 6969 - 6971
  • [9] Chiral chromium(III) porphyrins as highly enantioselective catalysts for hetero-Diels-Alder reactions between aldehydes and dienes
    Berkessel, A
    Ertürk, E
    Laporte, C
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) : 223 - 228
  • [10] A new dirhodium(II) carboxamidate complex as a chiral lewis acid catalyst for enantioselective hetero-Diels-Alder reactions
    Anada, M
    Washio, T
    Shimada, N
    Kitagaki, S
    Nakajima, M
    Shiro, M
    Hashimoto, S
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (20) : 2665 - 2668
12345