RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
![](/products/assets/desktop/img/oa-logo.png)
Synthesis 2015; 47(16): 2377-2384
DOI: 10.1055/s-0034-1380197
DOI: 10.1055/s-0034-1380197
special topic
An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence
Weitere Informationen
Publikationsverlauf
Received: 26. Februar 2015
Accepted: 12. März 2015
Publikationsdatum:
02. April 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201516/lookinside/thumbnails/ss-2015-c0127-st_10-1055_s-0034-1380197-1.jpg)
Abstract
An organocatalytic quadruple cascade initiated by a Friedel–Crafts-type reaction is described. The (S)-diphenylprolinol trimethylsilyl ether catalyzed reaction yields highly functionalized cyclohexenecarbaldehydes bearing a 1,1-bis[4-(dialkylamino)phenyl]ethene moiety and three contiguous stereogenic centers. The reaction tolerates various functional groups and all products are obtained with very good diastereoselectivity and with virtually complete enantiomeric excess.
Key words
organocatalysis - domino reaction - quadruple cascade - asymmetric catalysis - alkenylationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380197.
- Supporting Information
-
References
- 1a Marcia de Figueiredo R, Christmann M. Eur. J. Org. Chem. 2007; 2575
- 1b Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167
- 1c Marques-Lopez E, Herrera RP, Christmann M. Nat. Prod. Rep. 2010; 27: 1138
-
1d Rueping M, Dufour J, Schoepke FR. Green Chem. 2011; 13: 1084
- 2a Tietze LF. Chem. Rev. 1996; 96: 115
- 2b Tietze LF, Brasche G, Gericke K. Domino Reactions in Organic Synthesis . Wiley-VCH; Weinheim: 2006
- 2c Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134
- 2d Pellissier H. Tetrahedron 2006; 62: 1619
- 2e Chapman CJ, Frost CG. Synthesis 2007; 1
- 3a Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
- 3b Walji AM, MacMillan DW. Synlett 2007; 1477
- 3c Yu X, Wang W. Org. Biomol. Chem. 2008; 6: 2037
- 3d Lu L.-Q, Chen J.-R, Xiao W.-J. Acc. Chem. Res. 2012; 45: 1278
- 3e Pellissier H. Adv. Synth. Catal. 2012; 354: 237
- 3f Grossmann A, Enders D. Angew. Chem. Int. Ed. 2012; 51: 314
- 3g Goudedranche S, Raimondi W, Bugaut X, Constantieux T, Bonne D, Rodriguez J. Synthesis 2013; 45: 1909
- 3h Volla CM. R, Atodiresei I, Rueping M. Chem. Rev. 2014; 114: 2390
- 4a Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew. Chem. Int. Ed. 2008; 47: 6138
- 4b Nielsen M, Worgull D, Zweifel T, Gschwend B, Bertelsen S, Jørgensen KA. Chem. Commun. 2011; 47: 632
- 4c Sunoj RB. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2011; 1: 920
- 4d Jensen KL, Dickmeiss G, Jiang H, Albrecht Ł, Jørgensen KA. Acc. Chem. Res. 2012; 45: 248
- 5a Wang W, Li H, Wang J, Zu L. J. Am. Chem. Soc. 2006; 128: 10354
- 5b Enders D, Wang C, Raabe G. Synthesis 2009; 4119
- 5c Rueping M, Kuenkel A, Tato F, Bats JW. Angew. Chem. Int. Ed. 2009; 48: 3699
- 5d Wang C, Yang X, Raabe G, Enders D. Adv. Synth. Catal. 2012; 354: 2629
- 5e Zhang X, Song X, Li H, Zhang S, Chen X, Yu X, Wang W. Angew. Chem. Int. Ed. 2012; 51: 7282
- 5f Lefranc A, Guénée L, Alexakis A. Org. Lett. 2013; 15: 2172
- 5g Wu L, Wang Y, Song H, Tang L, Zhou Z, Tang C. Chem. Asian J. 2013; 8: 2204
- 5h Joie C, Deckers K, Enders D. Synthesis 2014; 46: 799
- 6a Enders D, Hüttl MR. M, Raabe G, Bats JW. Adv. Synth. Catal. 2008; 350: 267
- 6b Bencivenni G, Wu L.-Y, Mazzanti A, Giannichi B, Pesciaioli F, Song M.-P, Bartoli G, Melchiorre P. Angew. Chem. Int. Ed. 2009; 48: 7200
- 6c Urushima T, Sakamoto D, Ishikawa H, Hayashi Y. Org. Lett. 2010; 12: 4588
- 6d Dong L.-J, Fan T.-T, Wang C, Sun J. Org. Lett. 2013; 15: 204
- 6e Chatterjee I, Bastida D, Melchiorre P. Adv. Synth. Catal. 2013; 355: 3124
- 6f Enders D, Joie C, Deckers K, Raabe G. Chem. Eur. J. 2013; 19: 10818
- 6g Zou L.-H, Philipps AR, Raabe G, Enders D. Chem. Eur. J. 2015; 21: 1004
- 7a Kotame P, Hong B.-C, Liao J.-H. Tetrahedron Lett. 2009; 50: 704
- 7b Zhang F.-L, Xu A.-W, Gong Y.-F, Wei M.-H, Yang X.-L. Chem. Eur. J. 2009; 15: 6815
- 7c Enders D, Krüll R, Bettray W. Synthesis 2010; 567
- 7d Enders D, Wang C, Mukanova M, Greb A. Chem. Commun. 2010; 46: 2447
- 7e Jiang K, Jia Z.-J, Yin X, Wu L, Chen Y.-C. Org. Lett. 2010; 12: 2766
- 7f Rueping M, Haack K, Ieawsuwan W, Sunden H, Blanco M, Schoepke FR. Chem. Commun. 2011; 47: 3828
- 7g Enders D, Greb A, Deckers K, Selig P, Merkens C. Chem. Eur. J. 2012; 18: 10226
- 7h Erdmann N, Philipps AR, Atodiresei I, Enders D. Adv. Synth. Catal. 2013; 355: 847
- 7i Joie C, Deckers K, Raabe G, Enders D. Synthesis 2014; 46: 1539
- 7j Lee H.-J, Shyam PK, Yoon W, Yun H, Jang H.-Y. Synthesis 2014; 46: 1329
- 7k Liu L, Zhu Y, Huang K, Wang B, Chang W, Li J. Eur. J. Org. Chem. 2014; 4342
- 7l Raja A, Hong B.-C, Lee G.-H. Org. Lett. 2014; 16: 5756
- 7m Jhuo D.-H, Hong B.-C, Chang C.-W, Lee G.-H. Org. Lett. 2014; 16: 2724
- 8a Carlone A, Marigo M, North C, Landa A, Jorgensen KA. Chem. Commun. 2006; 4928
- 8b Enders D, Hüttl MR. M, Grondal C, Raabe G. Nature (London) 2006; 441: 861
- 8c Marigo M, Bertelsen S, Landa A, Jørgensen KA. J. Am. Chem. Soc. 2006; 128: 5475
- 8d Carlone A, Cabrera S, Marigo M, Jørgensen KA. Angew. Chem. Int. Ed. 2007; 46: 1101
- 8e Enders D, Hüttl MR. M, Runsink J, Raabe G, Wendt B. Angew. Chem. Int. Ed. 2007; 46: 467
- 8f Hayashi Y, Okano T, Aratake S, Hazelard D. Angew. Chem. Int. Ed. 2007; 46: 4922
- 8g Reyes E, Jiang H, Milelli A, Elsner P, Hazell RG, Jørgensen KA. Angew. Chem. Int. Ed. 2007; 46: 9202
- 8h Ramachary DB, Reddy YV, Prakash BV. Org. Biomol. Chem. 2008; 6: 719
- 8i Enders D, Jeanty M, Bats JW. Synlett 2009; 3175
- 8j Wang Y, Han R.-G, Zhao Y.-L, Yang S, Xu P.-F, Dixon DJ. Angew. Chem. Int. Ed. 2009; 48: 9834
- 8k Hong B.-C, Nimje RY, Lin C.-W, Liao J.-H. Org. Lett. 2011; 13: 1278
- 8l Ishikawa H, Sawano S, Yasui Y, Shibata Y, Hayashi Y. Angew. Chem. Int. Ed. 2011; 50: 3774
- 8m Mao Z, Jia Y, Xu Z, Wang R. Adv. Synth. Catal. 2012; 354: 1401
- 8n Ma C, Jia Z.-J, Liu J.-X, Zhou Q.-Q, Dong L, Chen Y.-C. Angew. Chem. Int. Ed. 2013; 52: 948
- 8o Ma C, Jia Z.-J, Liu J.-X, Zhou Q.-Q, Dong L, Chen Y.-C. Angew. Chem. Int. Ed. 2013; 52: 948
- 8p Zeng X, Ni Q, Raabe G, Enders D. Angew. Chem. Int. Ed. 2013; 52: 2977
- 9 Cui L, Zhu Y, Luo S, Cheng J.-P. Chem. Eur. J. 2013; 19: 9481
- 10 Cui L, Zhang L, Luo S, Cheng J.-P. Eur. J. Org. Chem. 2014; 3540
- 11a Fabian J, Nakazumi H, Matsuoka M. Chem. Rev. 1992; 92: 1197
- 11b Hünig S, Kemmer M, Wenner H, Barbosa F, Gescheidt G, Perepichka IF, Bäuerle P, Emge A, Peters K. Chem. Eur. J. 2000; 6: 2618
- 11c Shandura MP, Poronik YM, Kovtun YP. Dyes Pigm. 2005; 66: 171
- 12a Yoshida K, Koujiri T, Oga N, Ishiguro M, Kubo Y. J. Chem. Soc., Chem. Commun. 1989; 708
- 12b Matsuoka M, Hikida T, Murobushi K, Hosoda Y. J. Chem. Soc., Chem. Commun. 1993; 299
- 12c Son Y.-A, Kim S.-H. Dyes Pigm. 2007; 72: 403
- 13 Okamoto K, Tamura E, Ohe K. Angew. Chem. Int. Ed. 2013; 52: 10639
- 14a Tuemmler W, Wildi B. J. Org. Chem. 1958; 23: 1056
- 14b Shirinian VZ, Shimkin AA, Lonshakov DV, Mailyan AK, Lvov AG, Krayushkin MM. Synthesis 2012; 44: 527
- 15 Marigo M, Wabnitz TC, Fielenbach D, Jørgensen KA. Angew. Chem. Int. Ed. 2005; 44: 794
For selected reviews, see:
For selected recent examples, see:
For selected recent examples, see:
For selected examples, see: