Fun with (4+3)-Cycloadditions

Michael Harmata

doi:10.1055/s-0037-1610327

Synlett, Table of Contents

Synlett 2019; 30(05): 532-541
DOI: 10.1055/s-0037-1610327

account

Fun with (4+3)-Cycloadditions

Michael Harmata *

Department of Chemistry, University of Missouri-Columbia, 601 South College Avenue, Columbia, Missouri, 65211, USA Email: harmatam@missouri.edu

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Abstract

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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

Key words

(4+3)-cycloadditions - sulfones - organocatalysis - oxidopyridinium ions - allylic cations - dienes - asymmetric catalysis

Full Text

References

References and Notes
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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
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4 Harmata M, Gamlath CB. J. Org. Chem. 1988; 53: 6154
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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
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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
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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
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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
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?