Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2017; 49(03): 647-656
DOI: 10.1055/s-0036-1588604
DOI: 10.1055/s-0036-1588604
paper
Highly Enantioselective Michael Addition of Aromatic Ketones to Nitrodienes and the Application to the Synthesis of Chiral γ-Aminobutyric Acid
Further Information
Publication History
Received: 15 July 2016
Accepted after revision: 02 September 2016
Publication Date:
26 September 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201703/lookinside/thumbnails/ss-2016-h0499-op_10-1055_s-0036-1588604-1.jpg)
Abstract
A highly enantioselective Michael addition of aromatic ketones to α,β,γ,δ-unsaturated nitro compounds is described. In the presence of a chiral primary amine-thiourea based on dehydroabietic amine, γ-nitro ketones were obtained in excellent enantioselectivities (up to 95% ee) with up to 95% yield. In addition, this methodology has been successfully applied in the asymmetric synthesis of chiral 3-(aminomethyl)-5-phenylpentanoic acid.
Key words
chiral primary amine-thiourea - enantioselective catalysis - ketone - Michael addition - nitrodieneSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588604.
- Supporting Information
-
References
- 1a Ballini R. Stud. Nat. Prod. Chem. 1996; 19: 117
- 1b Sulzer-Mosse S, Alexakis A. Chem. Commun. 2007; 3123
- 1c Ballini R, Palmieria A, Righib P. Tetrahedron 2007; 63: 12099
- 1d Ballini R, Palmieri A, Barboni L. Chem. Commun. 2008; 2975
- 1e Ballini R, Petrini M. ARKIVOC 2009; (ix): 195
- 1f Ballini R, Gabrielli S, Palmieri A, Petrini M. Curr. Org. Chem. 2011; 15: 1482
- 2a Perlmutter P. Conjugate Addition Reactions in Organic Synthesis. Pergamon; Oxford: 1992
- 2b Gil M, Roman E, Serrano JA. Trends Org. Chem. 2001; 9: 17
- 2c Berner OM, Tedeschi L, Enders D. Eur. J. Org. Chem. 2002; 1877
- 2d Christoffers J, Baro A. Angew. Chem. Int. Ed. 2003; 42: 1688
- 2e Notz W, Tanaka F, Barbas CF. III. Acc. Chem. Res. 2004; 37: 580
- 2f Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713
- 2h Almasi D, Alonso DA, Nájera C. Tetrahedron: Asymmetry 2007; 18: 299
- 2i Tsogoeva SB. Eur. J. Org. Chem. 2007; 1701
- 2j Vicario JL, Badia D, Carrillo L. Synthesis 2007; 2065
- 2k Córdova A. Catalytic Asymmetric Conjugate Reactions . Wiley-VCH; Weinheim: 2010
- 2l Roca-Lopez D, Sadaba D, Delso I, Herrera RP, Tejero T, Merino P. Tetrahedron: Assymetry 2010; 21: 2561
- 2m Ji J.-X, Chan AS. C. Catalytic Asymmetric Synthesis . Wiley-VCH; Weinheim: 2010: 479
- 2n Zhang Y, Wang W. Catal. Sci. Technol. 2012; 2: 42
- 2o Serdyuk OV, Heckel CM, Tsogoeva SB. Org. Biomol. Chem. 2013; 11: 7051
- 2p Vicario JL, Reyes E, Carrillo L, Uria U. Comprehensive Organic Synthesis . Vol. 4. Pergamon; Oxford: 2014: 119
- 3a Ballini R, Araújo N, Gil MV, Román E, Serrano JA. Chem. Rev. 2013; 113: 3493
- 3b Tsakos M, Kokotos CG. Tetrahedron 2013; 69: 10199
- 4a List B, Pojarliev P, Martin HJ. Org. Lett. 2001; 3: 2423
- 4b Chua PJ, Tan B, Zeng X, Zhong G. Bioorg. Med. Chem. Lett. 2009; 19: 3915
- 4c Lu A, Gao P, Wu Y, Wang Y, Zhou Z, Tang C. Org. Biomol. Chem. 2009; 7: 3141
- 4d Zeng X, Zhong G. Synthesis 2009; 1545
- 4e Belot S, Quintard A, Krause N, Alexakis A. Adv. Synth. Catal. 2010; 352: 667
- 4f Lu A, Liu T, Wu R, Wang Y, Zhou Z, Wu P, Fang J, Tang C. Eur. J. Org. Chem. 2010; 5777
- 4g Li Z.-B, Luo S.-P, Guo Y, Xia A.-B, Xu D.-Q. Org. Biomol. Chem. 2010; 8: 2505
- 4h Chen J.-R, Fu L, Zou Y.-Q, Chang N.-J, Rong J, Xiao W.-J. Org. Biomol. Chem. 2011; 9: 5280
- 4i Quintard A, Langlois JB, Emery D, Mareda J, Guénée L, Alexakis A. Chem. Eur. J. 2011; 17: 13433
- 4j Lu A, Wu R, Wang Y, Zhou Z, Wu P, Fang J, Tang C. Eur. J. Org. Chem. 2011; 122
- 4k Lu A, Liu T, Wu R, Wang Y, Wu P, Zhou Z, Fang J, Tang C. J. Org. Chem. 2011; 76: 3872
- 4l He T, Wu X.-Y. Synth. Commun. 2012; 42: 667
- 4m Tsakos M, Trifonidou M, Kokotos CG. Tetrahedron 2012; 68: 8630
- 4n Singh S, Chimni SS. Tetrahedron: Asymmetry 2012; 23: 1068
- 4o Tsakos M, Elsegood MR. J, Kokotos CG. Chem. Commun. 2013; 49: 2219
- 4p Xia A.-B, Wu C, Xu D.-Q, Wang Y.-F, Du X.-H, Li Z.-B, Xu Z.-Y. J. Org. Chem. 2013; 78: 1254
- 4q Wang Y, Jiang M, Liu J.-T. Tetrahedron: Asymmetry 2014; 25: 212
- 4r Xia A.-B, Zhao L, Wang T, Zhang Y.-P, Zhang A.-G, Xu D.-Q, Xu Z.-Y. New J. Chem. 2015; 39: 355
- 4s Kaplaneris N, Koutoulogenis G, Raftopoulou M, Kokotos CG. J. Org. Chem. 2015; 80: 5464
- 5a He T, Qian J.-Y, Song H.-L, Wu X.-Y. Synlett 2009; 3195
- 5b Li B.-L, Wang Y.-F, Luo S.-P, Zhong A.-G, Li Z.-B, Du X.-H, Xu D.-Q. Eur. J. Org. Chem. 2010; 656
- 5c Ma H, Liu K, Zhang F.-G, Zhu C.-L, Nie J, Ma J.-A. J. Org. Chem. 2010; 75: 1402
- 5d Tsakos M, Kokotos CG. Eur. J. Org. Chem. 2012; 576
- 6a Jiang X, Zhang Y, Chan AS. C, Wang R. Org. Lett. 2009; 11: 153
- 6b Guo X.-T, Sha F, Wu X.-Y. Res. Chem. Intermed. 2016; 42: 6373
- 7 Guo X.-T, Shen J, Sha F, Wu X.-Y. Synthesis 2015; 47: 2063
- 8a Saito S, Nakadai M, Yamamoto H. Synlett 2001; 1245
- 8b Mase N, Tanaka F, Barbas CF. III. Org. Lett. 2003; 5: 4369
- 8c Mangion IK, Northrup AB, MacMillan DW. C. Angew. Chem. Int. Ed. 2004; 43: 6722
- 8d Gryko D, Zimnicka M, Lipinski R. J. Org. Chem. 2007; 72: 964
- 9a Jiang X, Zhang Y, Liu X, Zhang G, Lai L, Wu L, Zhang J, Wang R. J. Org. Chem. 2009; 74: 5562
- 9b Jiang X, Zhang Y, Wu L, Zhang G, Liu X, Zhang H, Fu D, Wang R. Adv. Synth. Catal. 2009; 351: 2096
- 9c Jiang X, Zhang G, Fu D, Cao Y, Shen F, Wang R. Org. Lett. 2010; 12: 1544
- 9d Jiang X, Wang Y, Zhang G, Fu D, Zhang F, Kai M, Wang R. Adv. Synth. Catal. 2011; 353: 1787
- 9e Cao Y, Jiang X, Liu L, Shen F, Zhang F, Wang R. Angew. Chem. Int. Ed. 2011; 50: 9124
- 9f Zhang G, Zhang Y, Yan J, Chen R, Wang S, Ma Y, Wang R. J. Org. Chem. 2012; 77: 878
- 9g Wu X.-Y, Shen J, Zhao X, Sha F. CN103421044, 2013
- 9h Shi X.-M, Dong W.-P, Zhu L.-P, Jiang X.-X, Wang R. Adv. Synth. Catal. 2013; 355: 3119
- 9i Wang L, Shi X.-M, Dong W.-P, Zhu L.-P, Wang R. Chem. Commun. 2013; 49: 3458
- 9j Jiang X, Zhu H, Shi X, Zhong Y, Li Y, Wang R. ChemCatChem 2013; 5: 2187
- 9k Zhao X, Kang T, Shen J, Sha F, Wu X.-Y. Chin. J. Chem. 2015; 32: 1333
- 10 Bryans JS, Horwell DC, Kneen CO, Wustrow DJ, Thorpe AJ. WO 9817627, 1998
For selected reviews, see:
For selected reviews, see:
For reviews, see:
For the organocatalytic asymmetric Michael addition of aliphatic ketones to nitrodienes, see:
For the organocatalytic asymmetric Michael addition of aromatic ketones to nitrodienes, see: