Synlett 2019; 30(05): 532-541
DOI: 10.1055/s-0037-1610327
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© Georg Thieme Verlag Stuttgart · New York

Fun with (4+3)-Cycloadditions

Department of Chemistry, University of Missouri-Columbia, 601 South College Avenue, Columbia, Missouri, 65211, USA   Email: [email protected]
› Author Affiliations
The work from my group described herein was supported by the ­National Science Foundation (CHE-1463724 for the most recent grant). Without this organization, I would not have had the career I have. I express my deepest gratitude to them for their help in accomplishing our research goals.
Further Information

Publication History

Received: 05 August 2018

Accepted after revision: 19 October 2018

Publication Date:
27 November 2018 (online)


Dedicated to the memory of my parents, Andrew and Bernadine Harmata

Abstract

This account describes how I began my adventure in the area of (4+3)-cycloadditions and then focuses on two ongoing projects: a new catalytic asymmetric (4+3)-cycloaddition and what might be described as the ‘rebirth’ of oxidopyridinium ion (4+3)-cycloaddition chemistry. References to other people’s work are made where appropriate.

1 Introduction

2 Asymmetric, Catalytic (4+3)-Cycloadditions

3 Oxidopyridinium Ions and (4+3)-Cycloadditions

4 Conclusions and the Future

 
  • References and Notes

  • 1 Denmark SE, Harmata MA. J. Am. Chem. Soc. 1982; 104: 4972
  • 2 Trost BM, Chadiri MR. J. Am. Chem. Soc. 1984; 106: 7260

    • Reviews on (4+3)-cycloadditions available in the mid-1980s:
    • 3a Mann J. Tetrahedron 1986; 42: 4611
    • 3b Hoffmann HM. R. Angew. Chem., Int. Ed. Engl. 1984; 23: 1
    • 3c Noyori R. Acc. Chem. Res. 1979; 12: 61
    • 3d Hoffmann HM. R. Angew. Chem., Int. Ed. Engl. 1973; 12: 819
  • 4 Harmata M, Gamlath CB. J. Org. Chem. 1988; 53: 6154
  • 5 Harmata M, Fletcher VR, Claassen RJ. II. J. Am. Chem. Soc. 1991; 113: 9861
  • 6 Harmata M, Sharma U. Org. Lett. 2000; 2: 2703
    • 7a Harmata M, Rashatasakhon P. Org. Lett. 2000; 2: 2913
    • 7b Harmata M, Elomari S, Barnes CL. J. Am. Chem. Soc. 1996; 118: 2860
    • 7c Harmata M, Elahmad S, Barnes CL. J. Org. Chem. 1994; 59: 1241
    • 8a Harmata M, Wacharasindhu S. Org. Lett. 2005; 7: 2563
    • 8b Harmata M, Bohnert GJ. Org. Lett. 2003; 5: 59
    • 8c Harmata M, Rashatasakhon P. Org. Lett. 2001; 3: 2533
    • 8d Harmata M, Shao L. Synthesis 1999; 1534
    • 9a Harmata M, Lee DR, Barnes CL. Org. Lett. 2005; 7: 1881
    • 9b Harmata M, Lee DR. J. Am. Chem. Soc. 2002; 124: 14328
    • 10a Harmata M, Kahraman M, Adenu G, Barnes CL. Heterocycles 2004; 62: 583
    • 10b Harmata M, Carter KW. Tetrahedron Lett. 1997; 38: 7985
  • 11 Harmata M, Gomes MG. Eur. J. Org. Chem. 2006; 2273
    • 12a Harmata M, Brackley JA, Barnes CL. Tetrahedron Lett. 2006; 47: 8151
    • 12b Harmata M, Ghosh SK, Hong X, Wacharasindhu S, Kirchhoefer P. J. Am. Chem. Soc. 2003; 125: 2058
    • 13a Huang J, Hsung RP. J. Am. Chem. Soc. 2005; 127: 50
    • 13b Villar L, Uria U, Martinez JI, Prieto L, Reyes E, Carrillo L, Vicario JL. Angew. Chem. Int. Ed. 2017; 56: 10535
    • 13c Banik SM, Levina A, Hyde AM, Jacobsen EN. Science 2017; 358: 761
    • 13d Gelis C, Levitre G, Merad J, Retailleau P, Neuville L, Masson G. Angew. Chem. Int. Ed. 2018; 57: 12121
  • 14 Ahrendt KA, Borths CJ, MacMillan DW. C. J. Am. Chem. Soc. 2000; 122: 4243
    • 15a Sun B.-F, Wang C.-L, Ding R, Xu J.-Y, Lin G.-Q. Tetrahedron Lett. 2011; 52: 2155
    • 15b Wang C.-L, Sun B.-F, Chen S.-G, Ding R, Lin G.-Q, Xu J.-Y, Shang Y.-J. Synlett 2012; 23: 263
    • 15c Wang J, Chen S.-G, Sun B.-F, Lin G.-Q, Shang Y.-J. Chem. Eur. J. 2013; 19: 2539
    • 15d Sun W.-B, Wang X, Sun B.-F, Zou J.-P, Lin G.-Q. Org. Lett. 2016; 18: 1219
  • 16 Krenske EH, Houk KN, Harmata M. J. Org. Chem. 2015; 80: 744
    • 17a Harmata M, Zheng P, Schreiner PR, Navarro-Vazquez A. Angew. Chem. Int. Ed. 2006; 45: 1966
    • 17b Harmata M, Rayanil K.-O. Synthesis 2007; 2370
    • 17c Harmata M, Zheng P, Schreiner PR, Navarro-Vazquez A. Tetrahedron Lett. 2007; 48: 5919
    • 17d Thomas JB, Waas JR, Harmata M, Singleton DA. J. Am. Chem. Soc. 2008; 130: 14544
  • 18 ‘Yet hope remains while the company is true’; the word has been used by at least one other: Dong S, Qin T, Hamel E, Beutler JA, Porco JA. J. Am. Chem. Soc. 2012; 134: 19782
  • 19 Harmata M, Brackley JA, Barnes CL. Tetrahedron Lett. 2006; 47: 8151
  • 20 Trost BM, Matelich MC. J. Am. Chem. Soc. 1991; 113: 9007
  • 21 Harmata M, Bohnert G, Barnes CL. Tetrahedron Lett. 2001; 42: 149

    • Selected reviews include:
    • 22a Yu B. Acc. Chem. Res. 2018; 51: 507
    • 22b Gu Y, Tan C, Gong J, Yang Z. Synlett 2018; 29: 1552
    • 22c Quach R, Furkert DP, Brimble MA. Org. Biomol. Chem. 2017; 15: 3098
    • 22d Echavarren AM, Hashmi AS. K, Toste FD. Adv. Synth. Catal. 2016; 358: 1347
  • 23 Aikawa H, Tago S, Umetsu K, Haginiwa N, Asao N. Tetrahedron 2009; 65: 1774
  • 24 Topinka M, Tata RR, Harmata M. Org. Lett. 2014; 16: 4476
  • 25 Harding AP, Wedge DC, Popelier PL. A. J. Chem. Inf. Model. 2009; 49: 1914
  • 26 Scherrer RA, Donovan SF. Anal. Chem. 2009; 81: 2768
    • 27a Jain P, Wang H, Houk KN, Antilla JC. Angew. Chem. Int. Ed. 2012; 51: 1391
    • 27b Zhang Z, Antilla JC. Angew. Chem. Int. Ed. 2012; 51: 11778
    • 27c Zhang Z, Jain P, Antilla JC. Angew. Chem. Int. Ed. 2011; 50: 10961
  • 28 He H, Chen L.-Y, Wong W.-Y, Chan W.-H, Lee AW. M. Eur. J. Org. Chem. 2010; 4181
  • 29 Liu C, Oblak EZ, Vander Wal MN, Dilger AK, Almstead DK, MacMillan DW. C. J. Am. Chem. Soc. 2016; 138: 2134
  • 30 Topinka M, Zawatzky K, Barnes CL, Welch CJ, Harmata M. Org. Lett. 2017; 19: 4106
  • 31 He CQ, Yu P, Lam Y.-H, Houk KN. Org. Lett. 2017; 19: 5685
  • 32 Dennis N, Ibrahim B, Katritzky AR. J. Chem. Soc., Perkin Trans. 1 1976; 2307
  • 33 Dennis N, Ibrahim B, Katritzky AR. J. Chem. Soc., Perkin Trans. 1 1976; 2296
  • 34 Dennis N, Katritzky AR, Rittner R. J. Chem. Soc., Perkin Trans. 1 1976; 2329
    • 35a Bejcek LP, Murelli RP. Tetrahedron 2018; 74: 2501
    • 35b Pellissier H. Adv. Synth. Catal. 2011; 353: 189
    • 35c Singh V, Krishna UM, Vikrant Trivedi GK. Tetrahedron 2008; 64: 3405
  • 36 Sammes PG, Street LJ. J. Chem. Soc., Perkin Trans. 1 1983; 1261
  • 37 Harmata M, Bohnert GJ. Org. Lett. 2003; 5: 59
    • 38a Ess DH, Wheeler SE, Iafe RG, Xu L, Celebi-Olcum N, Houk KN. Angew. Chem. Int. Ed. 2008; 47: 7592
    • 38b Thomas JB, Waas JR, Harmata M, Singleton DA. J. Am. Chem. Soc. 2008; 130: 14544
    • 38c Quadrelli P, Romano S, Toma L, Caramella P. J. Org. Chem. 2003; 68: 6035
    • 38d Caramella P, Quadrelli P, Toma L. J. Am. Chem. Soc. 2002; 124: 1130
  • 39 https://faculty.missouri.edu/~harmatam/fund.shtml
  • 40 Shirakawa S, Maruoka K. Angew. Chem. Int. Ed. 2013; 52: 4312
  • 41 A reviewer called this Account ‘…amazingly self-indulgent.’ But I did try to tone things down a bit; I took out the reference to Sister Mary Anne. In any case, I have been called much worse. I have attempted to humanize the scientific experience in this essay. Whether it offends, is considered unprofessional, or just completely fails, well, that is a chance I am willing to take. Another reviewer probably knew me well enough to recognize that there is method in the madness. Interestingly, while some relatives lauded the work; one described it as a ‘pity party’. All of this is of interest to me. Whom does one try to please when writing?