Synthetic Applications of Sulfur-based Chiral Auxiliaries in Asymmetric Syntheses

Authors

  • Horacio F. Olivo Division of Medicinal and Natural Products Chemistry. The University of Iowa. Iowa City, IA, USA http://orcid.org/0000-0002-8082-5285
  • Rosmarbel Morales-Nava Division of Medicinal and Natural Products Chemistry. The University of Iowa. Iowa City, IA, USA http://orcid.org/0000-0001-8118-4419

DOI:

https://doi.org/10.29356/jmcs.v63i3.527

Keywords:

thiazolidienthione, oxazolidinethione, chiral auxiliary, aldol reaction, natural products

Abstract

This mini-review intends to present one of the themes that has driven my research in developing methodology for the synthesis of natural products and important biologically active molecules. Sulfur-based chiral auxiliaries from aminoacids have been shown to have superior qualities in many cases to other well-known chiral auxiliaries. Some applications of these auxiliaries include acetate aldol reactions, resolution of racemic mixtures, Michael additions, intramolecular thio-Michael/aldol cyclization cascade reactions, and synthesis of natural products, including a new practical and efficient indene-based thiazolidienthione auxiliary.

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References

. Evans, D. A.; Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Mathre, D. J.; Bartroli, J. Pure Appl. Chem. 1981, 53, 1109-1127.

. Evans, D. A. Aldrichimica Acta 1982, 15, 23-32.

. Hutchinson, D. K. Curr. Top. Med. Chem. 2003, 3, 1021-1042.

. Farina, V.; Reeves, J. T.; Senanayake, C. H.; Song, J. J. Chem. Rev. 2006, 106, 2734-2793.

. Velazquez, F .; Olivo, H. F. Curr. Org. Chem. 2002, 6, 3 03-340.

. Ortiz, A .; Sansinenea, E. J. Sulf. Chem. 2007, 28, 109-147.

. Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894-902.

. Wu, Y.; Yang, Y.; Hu, Q. J. Org. Chem. 2004, 69, 3990-3992.

. Delaunay, D.; Toupet, L.; Le Corre, M. J. Org. Chem. 1995, 60, 6604-6607.

. Morales-Nava, R.; Fernández-Zertuche, M.; Ordóñez, M. Molecules 2011, 16, 8803-8814.

. Heravi, M. M.; Zadsirjan, V.; Farajpour, B. RSC Advances 2016, 6, 30498-30551.

. Evans, D. A.; Nelson, J. V.; Taber, T. R. "Stereoselective Aldol Condensations," in: Topics in Stereochemistry, Vol. 13, New York, 1982, 2.

. Mukaiyama, T. "The Directed Aldol Reaction," in Organic Reactions, New York, Vol. 28, 1982, 203.

. Heathcock, C. H. Asymmetric Synthesis; Morrion, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, part B, p 111.

. Gnas, I.; Glorius, F. Synthesis 2006, 12, 1899-1930.

. Evans, D. A.; Helmchen, G.; Rüping, M. (2007). "Chiral Auxiliaries in Asymmetric Synthesis". In Christmann, M. Asymmetric Synthesis — The Essentials. Wiley-VCH Verlag GmbH & Co. pp. 3-9.

. Evans, D. A.; Takacs, J. M.; McGee, R. L.; Ennis, M. D.; Mathre, D. J. Bartroli, J. Pure & Appl. Chem. 1981, 53, 1109-1127.

. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747-5750.

. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.

. Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391-2393.

. Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419.

. Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.

. Morales-Nava, R.; Fernández-Zertuche, M.; Ramírez-Solís, A. J. Mex. Chem. Soc. 2014, 58(2), 89-94.

. Romero-Ortega, M.; Colby, D. A.; Olivo, H. F. Tetrahedron Lett. 2002, 43, 6439-6441.

. Sone, H.; Kigosi, H.; Yamada, K. J. Org. Chem. 1996, 61, 8956-8960.

. Zampella, A.; D’Auria, M. V.; Minale, L.; Debitus, C.; Roussakis, C. J. Am. Chem. Soc. 1996, 118, 11085-11088.

. Soullez, D.; Ple, G.; Duhamel, L. J. Chem. Soc. Perkin Trans 1 1997, 1639-1645.

. Tello-Aburto, R.; Ochoa-Teran, A.; Olivo, H. F. Tetrahedron Lett. 2006, 47, 5915-5917.

. Teitelman, E. Am. J. Psychiat. 2001, 158, 970-971.

. Osorio-Lozada; Olivo, H. F. Tetrahedron: Asymmetry 2004, 15, 3811-3815.

. Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571.

. Olivo, H. F.; Tovar-Miranda, R.; Barragan, E. J. Org. Chem. 2006, 71, 3287-3290.

. Barragan, E.; Olivo, H. F.; Romero-Ortega, M.; Sarduy, S. J. Org. Chem. 2005, 70, 4214-4217.

. Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392.

. Evans, D. A.; Downey, C. W.; Shaw, T. J.; Tedrow, J. S. Org. Lett. 2002, 4, 1127.

. Rodriguez AD, Ramirez C. J. Nat. Prod. 2001, 64, 100-102.

. Molina-Salinas, G. M.; Rivas-Galindo, V. M.; Said-Fernandez, S.; Lankin, D. C.; Munoz, M. A.; Joseph-Nathan, P.; Pauli, G. F.; Waksman, N. J. Nat. Prod. 2011, 74, 1842-1850.

. Sabala, R.; Hernandez-Garcia, L.; Ortiz, A.; Romero, M.; Olivo, H. F. Org. Lett. 2010, 12, 4268-4270.

. Smith, T. E.; Djang, M.; Velander, A. J.; Downey, C. W.; Carroll, K. A.; van Alphen, S. Org. Lett. 2004, 6, 2317-2320.

. Rodriguez-Cardenas, E.; Sabala, R.; Romero-Ortega, M.; Ortiz, A.; Olivo, H. F. Org. Lett. 2012, 14, 238-240.

. Munive, L.; Rivas, V. M.; Ortiz, A.; Olivo, H. F. Org. Lett. 2012, 14, 3514-3517.

. Munive, L.; Dzakuma, S. A.; Olivo, H. F. Tetrahedron Lett. 2013, 54, 1230-1232.

. Palomo, C.; Oiarbide, M.; Dias, F.; Ortiz, A.; Linden, A. J. Am. Chem. Soc. 2001, 123, 5602-5603.

. Ortiz, A.; Quintero, L.; Hernandez, H.; Maldonado, S.; Mendoza, G.; Bernes, S. Tetrahedron Lett. 2003, 44, 1129-1132.

. Palomo, C.; Oiarbide, M.; Dias, F.; Lopez, R.; Linden, A. Angew. Chem. Int. Ed. 2004, 43, 3307-3310.

. Palomo, C.; Oiarbide, M.; Lopez, R.; Gonzalez, P. B.; Gomez-Bengoa, E.; Saa, J. M.; Linden. A. J. Am. Chem. Soc. 2006, 128, 15236-15247.

. Rivas, V. M.; Munive, L.; Olivo, H. F. Synlett 2014, 25, 876-880.

. Minor-Villar, L.; Tello-Aburto, R.; Olivo, H. F.; Fuentes, A.; Romero-Ortega, M. Synlett 2012, 23, 2835-2839.

. Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.; Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306.

. Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256.

. Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25.

. Zhang, Y.; Sammakia, T. Org. Lett. 2004, 6, 3139-3141.

. Crimmins, M. T.; Shamszad, M. Org. Lett. 2007, 9, 149-152.

. Gosh, A. K.; Duong, T. T.; McKee, S. P. J. Chem. Soc., Chem. Commun. 1992, 1673-1674.

. Osorio-Lozada, A.; Olivo, H. F. Org. Lett. 2008, 10, 617-620.

. Tello-Aburto, R.; Olivo, H. F. Org. Lett. 2008, 10, 2191-2194.

. Osorio-Lozada, A.; Olivo, H. F. J. Org. Chem. 2009, 74, 1360-1363.

. Cafieri, F.; Fattorusso, E.; Tagliatela-Scafati, O.; Di Rosa, M.; Ianaro, A. Tetrahedron 1999, 55, 13831-13840.

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Published

2019-10-17

Issue

Vol. 63 No. 3 (2019): Special Issue: Mexican Chemist Overseas

Section

Regular Articles

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