Relay Catalytic Cascade Hydrosiloxylation and Asymmetric Hetero-Diels–Alder Reaction

Nan Li; Dian-Feng Chen; Pu-Sheng Wang; Zhi-Yong Han; Liu-Zhu Gong

doi:10.1055/s-0033-1340905

Synthesis, Table of Contents

Synthesis 2014; 46(10): 1355-1361
DOI: 10.1055/s-0033-1340905

special topic

Relay Catalytic Cascade Hydrosiloxylation and Asymmetric Hetero-Diels–Alder Reaction

Nan Li

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)3606266 Email: gonglz@ustc.edu.cn

,

Dian-Feng Chen

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)3606266 Email: gonglz@ustc.edu.cn

,

Pu-Sheng Wang

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)3606266 Email: gonglz@ustc.edu.cn

,

Zhi-Yong Han

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)3606266 Email: gonglz@ustc.edu.cn

,

Liu-Zhu Gong*

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)3606266 Email: gonglz@ustc.edu.cn

› Author Affiliations

Abstract

All articles of this category

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.

Key words

Diels–Alder reaction - enantioselectivity - silicon - heterocycles - enynes

Full Text

References

References

Reviews:

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

Selected examples:

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

For recent reviews on the enantioselective construction of six-membered oxygenated heterocycles through catalytic asymmetric hetero-Diels–Alder reactions, see:

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

For representative examples of catalytic enantioselective hetero-Diels–Alder reactions of aldehydes with siloxy- and methoxydienes, see:

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

For reviews:

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

For early reports:

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

For recent examples:

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

Supplementary Material

Supporting Information

Primary Data

Primary Data