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Synthesis 2013; 45(12): 1641-1646
DOI: 10.1055/s-0033-1338705
DOI: 10.1055/s-0033-1338705
special topic
Catalytic Asymmetric Direct Vinylogous Michael Addition of γ-Aryl-Substituted Deconjugated Butenolides to Nitroolefins and N-Phenylmaleimide
Weitere Informationen
Publikationsverlauf
Received: 08. März 2013
Accepted after revision: 15. April 2013
Publikationsdatum:
08. Mai 2013 (online)

Abstract
Direct asymmetric vinylogous Michael reactions of γ-aryl-substituted deconjugated butenolides with nitroolefins and N-phenylmaleimide are described using bifunctional thiourea derivatives as the catalyst. The resulting butenolide derivatives containing adjacent quaternary and tertiary stereocenters are obtained in good yields (54–90%) and with excellent enantioselectivities (er up to 99:1) and high diastereoselectivities (dr up to >20:1).
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Das JP, Marek I. Chem. Commun. 2011; 47: 4593
- 1b Trost BM, Jiang C. Synthesis 2006; 369
- 1c Christoffers J, Baro A. Adv. Synth. Catal. 2005; 347: 1473
- 1d Christoffers J, Mann A. Angew. Chem. Int. Ed. 2001; 40: 4591
- 2a Igarashi Y, Ogura H, Furihata K, Oku N, Indananda C, Thamchaipenet A. J. Nat. Prod. 2011; 74: 670
- 2b Montagnon T, Tofi M, Vassilikogiannakis G. Acc. Chem. Res. 2008; 41: 1001
- 2c Shiomi K, Ui H, Suzuki H, Hatano H, Nagamitsu T, Takano D, Miyadera H, Yamashita T, Kita K, Miyoshi H, Harder A, Tomoda H, Ōmura S. J. Antibiot. 2005; 58: 50
- 3 For a non-asymmetric γ-arylation of butenolides, see: Hyde AM, Buchwald SL. Org. Lett. 2009; 11: 2663
- 4 Quintard A, Lefranc A, Alexakis A. Org. Lett. 2011; 13: 1540
- 5 Zhou L, Lin L, Ji J, Xie M, Liu X, Feng X. Org. Lett. 2011; 13: 3056
- 6 Huang X, Peng J, Dong L, Chen Y.-C. Chem. Commun. 2012; 48: 2439
- 7 Cui H.-L, Huang J.-R, Lei J, Wang Z.-F, Chen S, Wu L, Chen Y.-C. Org. Lett. 2010; 12: 720
- 8 Zhang W, Tan D, Lee R, Tong G, Chen W, Qi B, Huang K.-W, Tan C.-H, Jiang Z. Angew. Chem. Int. Ed. 2012; 51: 10069
- 9 Manna MS, Kumar V, Mukherjee S. Chem. Commun. 2012; 48: 5193
- 10 Manna MS, Mukherjee S. Chem. Eur. J. 2012; 18: 15277
- 11 Sonpatki VM, Herbert MR, Sandvoss LM, Seed AJ. J. Org. Chem. 2001; 66: 7283
- 12 Osman NA, Mahmoud AH, Allarà M, Niess R, Abouzid KA, Marzo VD, Abadi AH. Bioorg. Med. Chem. 2010; 18: 8463
For selected reviews on the generation of quaternary stereogenic centers, see:
For selected examples on butenolide as substructure in natural products, see: