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-00000083.xml
Synlett 2020; 31(06): 535-546
DOI: 10.1055/s-0039-1690777
DOI: 10.1055/s-0039-1690777
account
3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
Authors
This work was conducted with financial support from Università degli Studi di Milano, Italy (Piano Sostegno alla Ricerca - PSR2018 grant to SG).
Further Information
Publication History
Received: 21 October 2019
Accepted after revision: 03 December 2019
Publication Date:
07 January 2020 (online)
Published as part of the ISySyCat2019 Special Issue
Abstract
This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail.
1 Introduction
2 The BITIOPO Family
3 Enantioselective Opening of Epoxides
4 Enantioselective Allylation of Aldehydes
5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones
6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives
7 Conclusions
-
References
- 1 Kobayashi S, Nishio K. Tetrahedron Lett. 1993; 34: 3453
- 2a Denmark SE, Coe DM, Pratt NE, Griedel BD. J. Org. Chem. 1994; 59: 6161
- 2b Denmark SE, Fu J. J. Am. Chem. Soc. 2000; 122: 12021
- 2c Denmark SE, Stavenger RA. Acc. Chem. Res. 2000; 33: 432
- 2d Denmark SE, Heemstra JR, Beutner GL. Angew. Chem. Int. Ed. 2005; 44: 4682
- 2e Denmark SE, Beutner GL. Angew. Chem. Int. Ed. 2008; 47: 1560
- 2f Denmark SE, Eklov BM. Chemistry 2008; 14: 234
- 2g Denmark SE, Lee W. Chem. Asian J. 2008; 3: 327
- 2h Orito Y, Nakajima M. Synthesis 2006; 1391
- 2i Sugiura M, Nakajima M. Allylations of C–O and C–N Double Bonds and Related Reactions. In Comprehensive Chirality. Elsevier; 2012: 214
- 2j Kotani S, Sugiura M, Nakajima M. Chem. Rec. 2013; 13: 362
- 2k Nakajima M, Kotani S, Sugiura M. Synlett 2014; 25: 631
- 2l Benaglia M, Guizzetti S, Pignataro L. Coord. Chem. Rev. 2008; 252: 492
- 2m Beutner GL, Denmark SE. In Inventing Reactions, Topics in Organometallic Chemistry. Springer; Berlin, Heidelberg: 2013: 55
- 2n Rendler S, Oestreich M. Synthesis 2005; 1727
- 3 Denmark SE, Eklov BM, Yao PJ, Eastgate MD. J. Am. Chem. Soc. 2009; 131: 11770
- 4a Benaglia M, Guizzetti S, Rossi S. Silicate-Mediated Stereoselective Reactions Catalyzed by Chiral Lewis Bases. In Catalytic Methods in Asymmetric Synthesis. John Wiley & Sons, Inc; Weinheim: 2011: 579-624
- 4b Rossi S, Denmark SE. Lewis Base-Catalyzed, Lewis Acid-Mediated Reactions (n → σ*). In Lewis Base Catalysis in Organic Synthesis. Wiley-VCH; Weinheim: 2016: 1039-1076
- 4c Denmark SE, Beutner GL. Principles, Definitions, Terminology, and Orbital Analysis of Lewis Base-Lewis Acid Interactions Leading to Catalysis. In Lewis Base Catalysis in Organic Synthesis. Wiley-VCH; Weinheim: 2016: 31-54
- 4d Kočovský P, Malkov AV. Lewis Bases as Catalysts in the Reduction of Imines and Ketones with Silanes (n → σ*). In Lewis Base Catalysis in Organic Synthesis. Wiley-VCH; Weinheim: 2016: 1077-1112
- 4e Malkov AV, Kočovský P. Lewis Base-Catalyzed Reactions of SiX3-Based Reagents with C=O, C=N (n → σ*). In Lewis Base Catalysis in Organic Synthesis. Wiley-VCH; Weinheim: 2016
- 4f Wilson TW, Denmark SE. Reactions of Epoxides (n → σ*) . In Lewis Base Catalysis in Organic Synthesis . Wiley-VCH; Weinheim: 2016: 1113-1152
- 5 Short JD, Attenoux S, Berrisford DJ. Tetrahedron Lett. 1997; 38: 2351
- 6 Kobayashi S, Sugiura M, Ogawa C. Adv. Synth. Catal. 2004; 346: 1023
- 7 Nakajima M, Kotani S, Ishizuka T, Hashimoto S. Tetrahedron Lett. 2005; 46: 157
- 8 Denmark SE, Fu J. J. Am. Chem. Soc. 2003; 125: 2208
- 9a Oestreich M, Rendler S. Synthesis 2005; 1727
- 9b Chuit C, Corriu RJ. P, Reye C, Young JC. Chem. Rev. 1993; 93: 1371
- 10 Malkov AV, Kočovský P. Lewis Base-Catalyzed Reactions of SiX3-Based Reagents with C=O, C=N (n → σ*). In Lewis Base Catalysis in Organic Synthesis. Wiley-VCH; Weinheim: 2016: 1011-1038
- 11 Benaglia M, Rossi S. Org. Biomol. Chem. 2010; 8: 3824
- 12 Benincori T, Cesarotti E, Piccolo O, Sannicolò F. J. Org. Chem. 2000; 65: 2043
- 13 Simonini V, Benaglia M, Benincori T. Adv. Synth. Catal. 2008; 350: 561
- 14 Pu X, Qi X, Ready JM. J. Am. Chem. Soc. 2009; 131: 10364
- 15 Sugiura M, Sato N, Sonoda Y, Kotani S, Nakajima M. Chem. Asian J. 2010; 5: 478
- 16 Ohmaru Y, Sato N, Mizutani M, Kotani S, Sugiura M, Nakajima M. Org. Biomol. Chem. 2012; 10: 4562
- 17 Bonsignore M, Benaglia M, Cozzi F, Genoni A, Rossi S, Raimondi L. Tetrahedron 2012; 68: 8251
- 18 Chen J, Liu D, Fan D, Liu Y, Zhang W. Tetrahedron 2013; 69: 8161
- 19 Zhang P, Han Z, Wang Z, Ding K. Angew. Chem. Int. Ed. 2013; 52: 11054
- 20 Ogasawara M, Kotani S, Nakajima H, Furusho H, Miyasaka M, Shimoda Y, Wu WY, Sugiura M, Takahashi T, Nakajima M. Angew. Chem. Int. Ed. 2013; 52: 13798
- 21 Rossi S, Benaglia M, Genoni A. Tetrahedron 2014; 70: 2065
- 22 Sevrain N, Volle J.-N, Pirat J.-L, Ayad T, Virieux D. RSC Adv. 2017; 7: 52101
- 23 Sevrain N, Volle J.-N, Pirat J.-L, Ayad T, Virieux D. Eur. J. Org. Chem. 2018; 2267
- 24 Rossi S, Benaglia M, Cirilli R, Benincori T. Asymmetric Catal. 2015; 2: 17
- 25 Abbinante VM, Benaglia M, Rossi S, Benincori T, Cirilli R, Pierini M. Org. Biomol. Chem. 2019; 17: 7474
- 26 Ayad T, Gernet A, Pirat J.-L, Virieux D. Tetrahedron 2019; For some representative examples of recent works not involving the use of biheteroaromatic phosphine oxides, see: 75: 4385
- 27 Tokuoka E, Kotani S, Matsunaga H, Ishizuka T, Hashimoto S, Nakajima M. Tetrahedron: Asymmetry 2005; 16: 2391
- 28 Kotani S, Furusho H, Sugiura M, Nakajima M. Tetrahedron 2013; 69: 3075
- 29 Denmark SE, Barsanti PA, Beutner GL, Wilson TW. Adv. Synth. Catal. 2007; 349: 567
- 30 Kotani S, Hashimoto S, Nakajima M. Tetrahedron 2007; 63: 3122
- 31 Kotani S, Shimoda Y, Sugiura M, Nakajima M. Tetrahedron Lett. 2009; 50: 4602
- 32 Rossi S, Benaglia M, Genoni A, Benincori T, Celentano G. Tetrahedron 2011; 67: 158
- 33 Denmark SE, Fu J. J. Am. Chem. Soc. 2003; 125: 2208
- 34 Shimoda Y, Kotani S, Sugiura M, Nakajima M. Chem. Eur. J. 2011; 17: 7992
- 35 Genoni A, Benaglia M, Rossi S, Celentano G. Chirality 2013; 25: 643
- 36 Rossi S, Benaglia M, Cozzi F, Genoni A, Benincori T. Adv. Synth. Catal. 2011; 353: 848
- 37 Wilcox CS, Babston RE. J. Org. Chem. 1984; 49: 1451
- 38 Rossi S, Annunziata R, Cozzi F, Raimondi L. Synthesis 2015; 47: 2113