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 2014; 46(10): 1355-1361
DOI: 10.1055/s-0033-1340905
DOI: 10.1055/s-0033-1340905
special topic
Relay Catalytic Cascade Hydrosiloxylation and Asymmetric Hetero-Diels–Alder Reaction
Further Information
Publication History
Received: 27 January 2014
Accepted after revision: 12 February 2014
Publication Date:
17 March 2014 (online)
Abstract
The hybrid gold(I)/Brønsted acid binary catalyst system enables enynes to participate in an asymmetric relay catalytic cascade intramolecular hydrosiloxylation and asymmetric hetero-Diels–Alder reaction with fluorenyl glyoxylate.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
Primary Data
- for this article are available online at http://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI: 10.4125/pd0056th.
- Primary Data
-
References
- 1a Ooi T, Maruoka K In Comprehensive Asymmetric Catalysis . Vol. 3. Jacobsen EN, Yamamoto H. Springer; Berlin: 1999: 1237-1254
- 1b Jørgensen KA In Cycloaddition Reactions in Organic Synthesis . Kobayashi S, Jørgensen KA. Wiley-VCH; Weinheim: 2002: 151-186
- 1c Crimmins MT, Haley MW, O’Bryan EA. Org. Lett. 2011; 13: 4712
- 1d Kobayashi H, Kanematsu M, Yoshida M, Shishido K. Chem. Commun. 2011; 47: 7440
- 1e Trost BM, Frontier AJ, Thiel OR, Yang H, Dong G. Chem. Eur. J. 2011; 17: 9762
- 1f Trost BM, Seganish WM, Chung CK, Amans D. Chem. Eur. J. 2012; 18: 2948
- 2a Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668
- 2b Jørgensen KA. Eur. J. Org. Chem. 2004; 2093
- 2c Lin L, Liu X, Feng X. Synlett 2007; 2147
- 2d Merino P, Marqués-López E, Tejero T, Herrera RP. Synthesis 2010; 1
- 2e Núñez MG, García P, Moro RF, Díez D. Tetrahedron 2010; 66: 2089
- 2f Moyano A, Rios R. Chem. Rev. 2011; 111: 4703
- 3 Pellissier H. Tetrahedron 2009; 65: 2839
- 4a Dossetter AG, Jamison TF, Jacobsen EN. Angew. Chem. Int. Ed. 1999; 38: 2398
- 4b Mikami K, Motoyama Y, Terada M. J. Am. Chem. Soc. 1994; 116: 2812
- 4c Quitschalle M, Christmann M, Bhatt U, Kalesse M. Tetrahedron Lett. 2001; 42: 1263
- 4d Momiyama N, Tabuse H, Terada M. J. Am. Chem. Soc. 2009; 131: 12882
- 5a Hashmi AS. K. Chem. Rev. 2007; 107: 3180
- 5b Li Z, Brouwer C, He C. Chem. Rev. 2008; 108: 3239
- 5c Arcadi A. Chem. Rev. 2008; 108: 3266
- 5d Gorin DJ, Sherry BD, Toste FD. Chem. Rev. 2008; 108: 3351
- 6a Mizushima E, Hayashi T, Tanaka M. Org. Lett. 2003; 5: 3349
- 6b Luo Y, Li Z, Li C.-J. Org. Lett. 2005; 7: 2675
- 7a Loh CC. J, Enders D. Chem. Eur. J. 2012; 18: 10212
- 7b Hashmi AS. K, Hubbert C. Angew. Chem. Int. Ed. 2010; 49: 1010
- 7c Han Z.-Y, Xiao H, Chen X.-H, Gong L.-Z. J. Am. Chem. Soc. 2009; 131: 9182
- 7d Muratore ME, Holloway CA, Pilling AW, Storer RI, Trevitt G, Dixon DJ. J. Am. Chem. Soc. 2009; 131: 10796
- 7e Liu X.-Y, Che C.-M. Org. Lett. 2009; 11: 4204
- 7f Liu X.-Y, Xiao Y.-P, Siu F.-M, Ni L.-C, Chen Y, Wang L, Che C.-M. Org. Biomol. Chem. 2012; 10: 7208
- 7g Fleischer S, Werkmeister S, Zhou S, Junge K, Beller M. Chem. Eur. J. 2012; 18: 9005
- 7h Patil NT, Raut VS, Tella RB. Chem. Commun. 2013; 49: 570
- 7i Qian D, Zhang J. Chem. Eur. J. 2013; 19: 6984
- 7j Gregory AW, Jakubec P, Turner P, Dixon DJ. Org. Lett. 2013; 15: 4330
- 8a Wang C, Han Z.-Y, Luo H.-W, Gong L.-Z. Org. Lett. 2010; 12: 2266
- 8b Han Z.-Y, Guo R, Wang P.-S, Chen D.-F, Xiao H, Gong L.-Z. Tetrahedron Lett. 2011; 52: 5963
- 8c He Y.-P, Wu H, Chen D.-F, Yu J, Gong L.-Z. Chem. Eur. J. 2013; 19: 5232
- 8d Wu H, He Y.-P, Gong L.-Z. Adv. Synth. Catal. 2012; 354: 975
- 8e Wu H, He Y.-P, Gong L.-Z. Org. Lett. 2013; 15: 460
- 8f Wu X, Li M, Gong L.-Z. Acta Chim. Sin. 2013; 71: 1091
- 9 Han Z.-Y, Chen D.-F, Wang Y.-Y, Guo R, Wang P.-S, Wang C, Gong L.-Z. J. Am. Chem. Soc. 2012; 134: 6532
- 10 Wang P.-S, Li K.-N, Zhou X.-L, Wu X, Han Z.-Y, Guo R, Gong L.-Z. Chem. Eur. J. 2013; 19: 6234
- 11 A 73% yield of diene was isolated.
- 12 Kim SM, Park JH, Choi SY, Chung YK. Angew. Chem. Int. Ed. 2007; 46: 6172
- 13 Nakashima D, Yamamoto H. J. Am. Chem. Soc. 2006; 128: 9626
- 14 Johnson MT, Rensburg JM. J. V, Axelsson M, Ahlquist MS. G, Wendt OF. Chem. Sci. 2011; 2: 2373
- 15 Wang ZJ, Burks HE, Toste FD. J. Am. Chem. Soc. 2011; 133: 8486
Reviews:
Selected examples:
For recent reviews on the enantioselective construction of six-membered oxygenated heterocycles through catalytic asymmetric hetero-Diels–Alder reactions, see:
For representative examples of catalytic enantioselective hetero-Diels–Alder reactions of aldehydes with siloxy- and methoxydienes, see:
For reviews:
For early reports:
For recent examples: