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: harmatam@missouri.edu
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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.
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Publikationsverlauf

Received: 05. August 2018

Accepted after revision: 19. Oktober 2018

Publikationsdatum:
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

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    • Reviews on (4+3)-cycloadditions available in the mid-1980s:
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    • 7a Harmata M, Rashatasakhon P. Org. Lett. 2000; 2: 2913
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  • 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
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    • Selected reviews include:
    • 22a Yu B. Acc. Chem. Res. 2018; 51: 507
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  • 24 Topinka M, Tata RR, Harmata M. Org. Lett. 2014; 16: 4476
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    • 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
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  • 31 He CQ, Yu P, Lam Y.-H, Houk KN. Org. Lett. 2017; 19: 5685
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    • 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
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  • 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?