Diaryl Prolinols in Stereoselective Catalysis and Synthesis: An Update
Corresponding Author
Dr. Sara Meninno
Dipartimento di Chimica e Biologia, University of Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy
Search for more papers by this authorChiara Volpe
Dipartimento di Chimica e Biologia, University of Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy
Search for more papers by this authorCorresponding Author
Prof. Dr. Alessandra Lattanzi
Dipartimento di Chimica e Biologia, University of Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy
Search for more papers by this authorCorresponding Author
Dr. Sara Meninno
Dipartimento di Chimica e Biologia, University of Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy
Search for more papers by this authorChiara Volpe
Dipartimento di Chimica e Biologia, University of Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy
Search for more papers by this authorCorresponding Author
Prof. Dr. Alessandra Lattanzi
Dipartimento di Chimica e Biologia, University of Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy
Search for more papers by this authorGraphical Abstract
On the way to synthetic applications: this minireview highlights recent developments of readily available α,α-diaryl prolinols in asymmetric catalysis and synthesis. At this stage, their “catalytic evolution” has reached the point of versatile and convenient employment in key-steps for the total synthesis of bioactive and natural compounds.
Abstract
Discovered more than one decade ago, α,α-diaryl prolinols, most of them commercially available compounds, demonstrated to be distinctive organocatalysts in asymmetric synthesis. Their application successfully spanned across different carbon-carbon or carbon-heteroatom bond forming reactions and cascade processes, exploiting covalent and noncovalent activation of the reagents. In this minireview, the advances from 2013 up to the end of 2018 in α,α-diaryl prolinols promoted stereoselective catalysis and synthesis of biologically active compounds, are illustrated.
Conflict of interest
The authors declare no conflict of interest.
References
- 1For recent reviews, see:
- 1aS. Afewerki, A. Córdova, Chem. Rev. 2016, 116, 13512–13570;
- 1bY. Deng, S. Kumar, H. Wang, Chem. Commun. 2014, 50, 4272–4284;
- 1cZ. Du, Z. Shao, Chem. Soc. Rev. 2013, 42, 1337–1378.
- 2For recent reviews, see:
- 2aM. Silvi, P. Melchiorre, Nature 2018, 554, 41–49;
- 2bI. K. Sideri, E. Voutyritsa, C. G. Kokotos, Org. Biomol. Chem. 2018, 16, 4596–4614.
- 3
- 3aAsymmetric Organocatalysis: from Biomimetic Concepts to Applications in Asymmetric Synthesis, (Eds.: A. Berkessel, H. Groeger), Wiley-VCH, 2005;
- 3bD. W. C. MacMillan, Nature 2008, 455, 304–308.
- 4
- 4aB. S. Donslund, T. K. Johansen, P. H. Poulsen, K. S. Halskov, K. A. Jørgensen, Angew. Chem. Int. Ed. 2015, 54, 13860–13874;
Angew. Chem. 2015, 127, 14066–14081;
10.1002/ange.201503920 Google Scholar
- 4bG. J. Reyes-Rodríguez, N. M. Rezayee, A. Vidal-Albalat, K. A. Jørgensen, Chem. Rev. 2019, 119, 4221–4260.
- 5
- 5aA. Lattanzi, Chem. Commun. 2009, 1452–1463;
- 5bS. Meninno, A. Lattanzi, Chem. Commun. 2013, 49, 3821–3832.
- 6
- 6aG. Zhong, J. Fan, C. F. Barbas III, Tetrahedron Lett. 2004, 45, 5681–5684;
- 6bY. Hayashi, T. Itoh, S. Aratake, H. Ishikawa, Angew. Chem. Int. Ed. 2008, 47, 2082–2084;
Angew. Chem. 2008, 120, 2112–2114.
10.1002/ange.200704870 Google Scholar
- 7J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjarsgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 18296–18304.
- 8
- 8aJ. Burés, A. Armstrong, D. G. Blackmond, Acc. Chem. Res. 2016, 49, 214–222;
- 8bT. Földes, Á. Madarász, Á. Révész, Z. Dobi, S. Varga, A. Hamza, P. R. Nagy, P. M. Pihko, I. Pápai, J. Am. Chem. Soc. 2017, 139, 17052–17063;
- 8cD. Seebach, X. Sun, M.-O. Ebert, W. B. Schweizer, N. Purkayastha, A. K. Beck, J. Duschmalé, H. Wennemers, Helv. Chim. Acta 2013, 96, 799–852.
- 9
- 9aY. Hayashi, S. Samanta, T. Itoh, H. Ishikawa, Org. Lett. 2008, 10, 5581–5583;
- 9bT. Itoh, H. Ishikawa, Y. Hayashi, Org. Lett. 2009, 11, 3854–3857;
- 9cUrushima, Y. Yasui, H. Ishikawa, Y. Hayashi, Org. Lett. 2010, 12, 2966–2969;
- 9dY. Hayashi, Y. Yasui, T. Kawamura, M. Kojima, H. Ishikawa, Synlett 2011, 485–488;
- 9eY. Hayashi, Y. Yasui, T. Kawamura, M. Kojima, H. Ishikawa, Angew. Chem. Int. Ed. 2011, 50, 2804–2807; Angew. Chem. 2011, 123, 2856–2859;
- 9fY. Hayashi, Y. Yasui, M. Kojima, T. Kawamura, H. Ishikawa, Chem. Commun. 2012, 48, 4570–4572.
- 10B. Alcaide, P. Almendros, Angew. Chem. Int. Ed. 2008, 47, 4632–4634;
Angew. Chem. 2008, 120, 4710–4712.
10.1002/ange.200801231 Google Scholar
- 11Y. Qiao, Q. Chen, S. Lin, B. Ni, A. D. Headley, J. Org. Chem. 2013, 78, 2693–2697.
- 12Y. Hayashi, M. Kojima, ChemCatChem 2013, 5, 2883–2885.
- 13Y. Hayashi, M. Kojima, Y. Yasui, Y. Kanda, T. Mukaiyama, H. Shomura, D. Nakamura, Ritmaleni, I. Sato, ChemCatChem 2013, 5, 2887–2892.
- 14E. Gómez-Bengoa, J. M. García, S. Jiménez, I. Lapuerta, A. Mielgo, J. M. Odriozola, I. Otazo, J. Razkin, I. Urruzuno, S. Vera, M. Oiarbide, C. Palomo, Chem. Sci. 2013, 4, 3198–3204.
- 15Y. Hayashi, K. Nishino, I. Sato, Chem. Lett. 2013, 42, 1294–1296.
- 16Y. Yasui, M. Benohoud, I. Sato, Y. Hayashi, Chem. Lett. 2014, 43, 556–558.
- 17
- 17aR. K. Boeckman Jr, J. R. Miller, Org. Lett. 2009, 11, 4544–4547;
- 17bR. K. Boeckman Jr, K. F. Biegasiewicz, D. J. Tusch, J. R. Miller, J. Org. Chem. 2015, 80, 4030–4045.
- 18
- 18aM. Kumar, B. A. Shah, S. C. Taneja, Adv. Synth. Catal. 2011, 353, 1207–1212;
- 18bX. Fan, C. Rodríguez-Escrich, S. Sayalero, M. A. Pericàs, Chem. Eur. J. 2013, 19, 10814–10817.
- 19M. Kumar, A. Kumar, M. Rizvi, M. Mane, K. Vanka, S. C. Taneja, B. A. Shah, Eur. J. Org. Chem. 2014, 24, 5247–5255.
- 20C. R. Müller, I. Meiners, P. Domínguez de María, RSC Adv. 2014, 4, 46097–46101.
- 21Y. Yasui, K. Ogata, I. Sato, Y. Hayashi, Adv. Synth. Catal. 2014, 356, 3106–3118.
- 22X. Fan, C. Rodríguez-Escrich, S. Wang, S. Sayalero, M. A. Pericàs, Chem. Eur. J. 2014, 20, 13089–13093.
- 23S. Wang, C. Rodríguez-Escrich, X. Fan, M. A. Pericàs, Tetrahedron 2018, 74, 3943–3946.
- 24Y. Hayashi, S. Watanabe, Y. Yasui, S. Umemiya, ChemCatChem 2015, 7, 1646–1649.
- 25F. Zhang, N. Su, Y. Gong, Synlett 2006, 1703–1706.
- 26Y. Hayashi, D. Nakamura, Y. Yasui, K. Iwasaki, H. Chiba, Adv. Synth. Catal. 2016, 358, 2345–2351.
- 27Y. Hayashi, T. Saitoh, H. Arase, G. Kawauchi, N. Takeda, Y. Shimasaki, I. Sato, Chem. Eur. J. 2018, 24, 4909–4915.
- 28P. A. Evans, A. Grisin, M. J. Lawler, J. Am. Chem. Soc. 2012, 134, 2856–2859.
- 29For selected reviews, see:
- 29aT. A. Palazzo, R. Mose, K. A. Jørgensen, Angew. Chem. Int. Ed. 2017, 56, 10033–10038;
Angew. Chem. 2017, 129, 10165–10171;
10.1002/ange.201701085 Google Scholar
- 29bY. Deng, Q.-Q. Cheng, M. P. Doyle, Synlett 2017, 28, 1695–1706;
- 29cV. Eschenbrenner-Lux, K. Kumar, H. Waldmann, Angew. Chem. Int. Ed. 2014, 53, 11146–11157;
Angew. Chem. 2014, 126, 11326–11337;
10.1002/ange.201404094 Google Scholar
- 29dE. J. Corey, Angew. Chem. Int. Ed. 2002, 41, 1650–1667;
10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO;2-B CASPubMedWeb of Science®Google ScholarAngew. Chem. 2002, 114, 1724–1741.10.1002/1521-3757(20020517)114:10<1724::AID-ANGE1724>3.0.CO;2-Q Google Scholar
- 30L.-W. Qi, Y. Yuan, Y.-Y. Gui. Y. Zhang, F. Chen, F. Tian, L. Peng, L.-X. Wang, Org. Lett. 2014, 16, 6436–6439.
- 31A. Raja, B.-C. Hong, J.-H. Liao, G.-H. Lee, Org. Lett. 2016, 18, 1760–1763.
- 32For a recent review, see: L. Klier, F. Tur, P. H. Poulsen, K. A. Jørgensen, Chem. Soc. Rev. 2017, 46, 1080–1102.
- 33For reviews, see:
- 33aP. Chauhan, S. Mahajan, D. Enders, Chem. Commun. 2015, 51, 12890–12907;
- 33bV. Kumar, K. Kaur, G. K. Gupta, A. K. Sharma, Eur. J. Med. Chem. 2013, 69, 735–753.
- 34
- 34aH. Jiang, Ł. Albrecht, K. A. Jørgensen, Chem. Sci. 2013, 4, 2287–2300;
- 34bŁ. Albrecht, G. Dickmeiss, C. F. Weise, C. Rodríguez-Escrich, K. A. Jørgensen, Angew. Chem. Int. Ed. 2012, 51, 13109–13113;
Angew. Chem. 2012, 124, 13286–13290.
10.1002/ange.201207122 Google Scholar
- 35S. Wang, C. Rodriguez-Escrich, M.-A. Pericàs, Org. Lett. 2016, 18, 556–559.
- 36For selected recent reviews, see:
- 36aB. Bdiri, B.-J. Zhao, Z.-M. Zhou, Tetrahedron: Asymmetry 2017, 28, 876–899;
- 36bJ. Otero-Fraga, M. Montesinos-Magraner, A. Mendoza, Synthesis 2017, 49, 802–809;
- 36cJ. Adrio, J. C. Carretero, Chem. Commun. 2014, 50, 12434–12446.
- 37J. L. Vicario, S. Reboredo, D. Badia, L. Carrillo, Angew. Chem. Int. Ed. 2007, 46, 5168–5170;
Angew. Chem. 2007, 119, 5260–5262.
10.1002/ange.200700988 Google Scholar
- 38S. Reboredo, L. Vicario, L. Carrillo, E. Reyes, U. Uria, Synthesis 2013, 2669–2678.
- 39S. Reboredo, A. García-Marijuan, U. Uria, E. Reyes, L. Carrillo, I. Ugarriza, J- L. Vicario, Org. Chem. Front. 2018, 15, 933–942.
- 40D. L. N. G. Surleraux, A. Tahri, W. G. Verschueren, G. M. E. Pille, H. A. de Kock, T. H. M. Jonckers, A. Peeters, S. De Meyer, H. Azijn, R. Pauwels, M.-P. de Bethune, N. M. King, M. Prabu-Jeyabalan, C. A. Schiffer, P. B. T. P. Wigerinck, J. Med. Chem. 2005, 48, 1813–1822.
- 41
- 41aA. K. Ghosh, Y. Chen, Tetrahedron Lett. 1995, 36, 505–508;
- 41bM. Uchiyama, M. Hirai, M. Nagata, R. Katoh, R. Ogawa, A. Ohta, Tetrahedron Lett. 2001, 42, 4653–4656;
- 41cA. K. Ghosh, W. J. Thompson, P. M. D. Fitzgerald, J. C. Culberson, M. G. Axel, S. P. McKee, J. R. Huff, P. S. Anderson, J. Med. Chem. 1994, 37, 2506–2508;
- 41dP. J. L. M. Quaedflieg, B. R. R. Kesteleyn, P. B. T. P. Wigerinck, N. M. F. Goyvaerts, R. J. Vijn, C. S. M. Liebregts, J. H. M. H. Kooistra, C. Cusan, Org. Lett. 2005, 7, 5917–5920.
- 42Y. Hayashi, T. Aikawa, Y. Shimasaki, H. Okamoto, Y. Tomioka, T. Miki, M. Takeda, T. Ikemoto, Org. Process Res. Dev. 2016, 20, 1615–1620.
- 43Y. Matsumoto, K. Hibino, M. Yonaga, H. Kakeya, Y. Hayashi, Org. Lett. 2016, 18, 3382–3385.
- 44A. M. Sarkale, A. Kumar, C. Appayee, J. Org. Chem. 2018, 83, 4167–4172.
- 45
- 45aJ. M. Crawforth, J. Fawcett, B. J. Rawlings, J. Chem. Soc. Perkin Trans. 1 1998, 1721–1726;
- 45bK. Mori, N. Chiba , Eur. J. Org. Chem. 1989, 957–962;
- 45cA. Comini, C. Forzato, P. Nitti, G. Pitacco, E. Valentin, Tetrahedron: Asymmetry 2004, 15, 617–625.
- 46P. Chauhan, S. Mahajan, D. Enders, Chem. Rev. 2014, 114, 8807–8864.
- 47L. Fang, A. Lin, Y. Shi, Y. Cheng, C. Zhu, Tetrahedron Lett. 2014, 55, 387–389.
- 48L. Fang, A. Lin, H. Hu, C. Zhu, Chem. Eur. J. 2009, 15, 7039–7043.