C–H Insertion Reactions of Donor/Donor Carbenes: Inception, Investigation, and Insights

Jared T. Shaw

doi:10.1055/s-0039-1691738

Synlett, Table of Contents

Synlett 2020; 31(09): 838-844
DOI: 10.1055/s-0039-1691738

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C–H Insertion Reactions of Donor/Donor Carbenes: Inception, Investigation, and Insights

Jared T. Shaw ∗

Department of Chemistry, One Shields Ave, University of California, Davis, CA 95166, USA Email: jtshaw@ucdavis.edu

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Abstract

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Abstract

Insertion reactions of donor/donor carbenes have emerged from obscurity to become a versatile method for the synthesis of a variety of cyclic structures with excellent control of diastereo- and enantioselectivity. This Account describes the origin of this project as part of a natural product synthesis and the ensuing decade of reaction development that has resulted in new asymmetric methods as well as intriguing tangential observations.

Key words

C–H insertion - carbenes - rhodium - asymmetric catalysis

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References

References
1 Gibbons S. Nat. Prod. Rep. 2004; 21: 263
2 Sato M, Tsuchiya H, Miyazaki T, Ohyama M, Tanaka T, Iinuma M. Lett. Appl. Microbiol. 1995; 21: 219
3 Davies HM. L. J. Org. Chem. 2019; 84: 12722
4 Deng Y, Qiu H, Srinivas HD, Doyle MP. Curr. Org. Chem. 2016; 20: 61
5 Eberlein TH, West FG, Tester RW. J. Org. Chem. 1992; 57: 3479
6 Park YS, Grove CI, González-López M, Urgaonkar S, Fettinger JC, Shaw JT. Angew. Chem. Int. Ed. 2011; 50: 3730
7 Cheung W.-H, Zheng S.-L, Yu W.-Y, Zhou G.-C, Che C.-M. Org. Lett. 2003; 5: 2535
8 Javed MI, Brewer M. Org. Synth. 2008; 85: 189
9 Soldi C, Lamb KN, Squitieri RA, Gonzalez-Lopez M, Di Maso MJ, Shaw JT. J. Am. Chem. Soc. 2014; 136: 15142
10 Lamb KN, Squitieri RA, Chintala SR, Kwong AJ, Balmond EI, Soldi C, Dmitrenko O, Reis MC, Chung R, Addison JB, Fettinger JC, Hein JC, Tantillo DJ, Fox JM, Shaw JT. Chem. Eur. J. 2017; 23: 11843
11 Quiclet-Sire B, Zard SZ. Chem. Commun. 2006; 1831
12 van Alphen J. Recl. Trav. Chim. Pays-Bas 1943; 62: 485
13 van Alphen J. Recl. Trav. Chim. Pays-Bas 1943; 62: 491
14 Huttel R, Riedl J, Martin H, Franke K. Chem. Ber. 1960; 93: 1425
15 Padwa A, Goldstein SI. Can. J. Chem. 1984; 62: 2506
16 Zheng Y, Qiu L, Hong K, Dong S, Xu X. Chem. Eur. J. 2018; 24: 6705
17 Dimirjian CA, Castineira Reis M, Balmond EI, Turman NC, Rodriguez EP, Di Maso MJ, Fettinger JC, Tantillo DJ, Shaw JT. Org. Lett. 2019; 21: 7209
18 Furrow ME, Myers AG. J. Am. Chem. Soc. 2004; 126: 12222
19 Squitieri RA, Shearn-Nance GP, Hein JE, Shaw JT. J. Org. Chem. 2016; 81: 5278
20 Souza LW, Squitieri RA, Dimirjian CA, Hodur BM, Nickerson LA, Penrod CN, Cordova J, Fettinger JC, Shaw JT. Angew. Chem. Int. Ed. 2018; 57: 15213
21 Munro DP, Sharp JT. Tetrahedron Lett. 1980; 21: 4109
22 Blake AJ, Harding M, Sharp JT. Tetrahedron Lett. 1988; 29: 6361
23 Ito M, Kondo Y, Nambu H, Anada M, Takeda K, Hashimoto S. Tetrahedron Lett. 2015; 56: 1397
24 Nickerson LA, Bergstrom BD, Gao M, Shiue Y.-S, Laconsay CJ, Culberson MR, Knauss WA, Fettinger JC, Tantillo DJ, Shaw JT. Chem. Sci. 2020; 11: 494