Synthesis and α-Functionalisation of Cyclic Imines

Ze Kuang; Xiao-Bo Ding; Daniel P. Furkert; Margaret A. Brimble

doi:10.1055/a-2251-4145

Synlett, Table of Contents

Synlett 2024; 35(15): 1813-1816
DOI: 10.1055/a-2251-4145

letter

Synthesis and α-Functionalisation of Cyclic Imines

Authors

Ze Kuang

^aSchool of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand
Xiao-Bo Ding

^aSchool of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand

^bThe Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds Street, Auckland, 1010, New Zealand
Daniel P. Furkert

^aSchool of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand

^bThe Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds Street, Auckland, 1010, New Zealand
Margaret A. Brimble ∗

^aSchool of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand

^bThe Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds Street, Auckland, 1010, New Zealand

Abstract

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Abstract

α-Functionalisation of cyclic imines is explored. The cyclic imine substrates are synthesised from their respective halonitrile precursors using a nucleophilic addition/cyclisation sequence. Selective monohalogenation of the cyclic imines yields α-haloimines, which serve as a platform to obtain various α-hydroxyimine derivatives. In addition, an unusual tautomerisation and oxidation sequence is observed in the attempted preparation of α-hydroxyimines.

Key words

cyclic imine - spiroimine - α-functionalisation - α-hydroxyimine - α-bromoimine

Full Text

References

References
1 Guéret SM, Brimble MA. Nat. Prod. Rep. 2010; 27: 1350
2 Hu T, Curtis JM, Walter JA, Wright JL. Tetrahedron Lett. 1996; 37: 7671
3 Rundberget T, Aasen JA. B, Selwood AI, Miles CO. Toxicon 2011; 58: 700
4 Roach JS, LeBlanc P, Lewis NI, Munday R, Quilliam MA, MacKinnon SL. J. Nat. Prod. 2009; 72: 1237
5 Takada N, Umemura N, Suenaga K, Chou T, Nagatsu A, Haino T, Yamada K, Uemura D. Tetrahedron Lett. 2001; 42: 3491
6 Selwood AI, Miles CO, Wilkins AL, van Ginkel R, Munday R, Rise F, McNabb P. J. Agric. Food Chem. 2010; 58: 6532
7 Seki T, Satake M, Mackenzie L, Kaspar HF, Yasumoto T. Tetrahedron Lett. 1995; 36: 7093
8 Miles CO, Wilkins AL, Stirling DJ, MacKenzie AL. J. Agric. Food Chem. 2000; 48: 1373
9 Miles CO, Wilkins AL, Stirling DJ, MacKenzie AL. J. Agric. Food Chem. 2003; 51: 4838
10 Takada N, Umemura N, Suenaga K, Uemura D. Tetrahedron Lett. 2001; 42: 3495
11 Lu C.-K, Lee G.-H, Huang R, Chou H.-N. Tetrahedron Lett. 2001; 42: 1713
12 Hermawan I, Higa M, Hutabarat PU. B, Fujiwara T, Akiyama K, Kanamoto A, Haruyama T, Kobayashi N, Higashi M, Suda S. Mar. Drugs 2019; 17: 353
13 Selwood AI, Wilkins AL, Munday R, Shi F, Rhodes LL, Holland PT. Tetrahedron Lett. 2013; 54: 4705
14 Fribley AM, Xi Y, Makris C, Alves-de-Souza C, York R, Tomas C, Wright JL, Strangman WK. ACS Med. Chem. Lett. 2018; 10: 175
15 Brooke DG, Cervin G, Champeau O, Harwood DT, Pavia H, Selwood AI, Svenson J, Tremblay LA, Cahill PL. Biofouling 2018; 34: 950
16 Buttery R, Ling LC, Juliano BO. Chem. Ind. (London) 1982; 23: 958
17 Buttery RG, Ling LC, Juliano BO, Turnbaugh JG. J. Agric. Food Chem. 1983; 31: 823
18 Adams A, De Kimpe N. Chem. Rev. 2006; 106: 2299
19 Fuganti C, Gatti FG, Serra S. Tetrahedron 2007; 63: 4762
20 Behr J.-B. Tetrahedron Lett. 2009; 50: 4498
21 Xu F, Chung JY, Moore JC, Liu Z, Yoshikawa N, Hoerrner RS, Lee J, Royzen M, Cleator E, Gibson AG. Org. Lett. 2013; 15: 1342
22 Williams SG, Bhadbhade M, Bishop R, Ung AT. Tetrahedron 2017; 73: 116
23 Voskressensky LG, Borisova TN, Matveeva MD, Khrustalev VN, Titov AA, Aksenov AV, Dyachenko SV, Varlamov AV. Tetrahedron Lett. 2017; 58: 877
24 Tang J, Li W, Chiu TY, Martinez-Pena F, Luo Z, Chong CT, Wei Q, Gazaniga N, West TJ, See YY, Lairson LL, Parker CG, Baran PS. Nature 2023; 622: 507
25 Tehrani KA, Borremans D, De Kimpe N. Tetrahedron 1999; 55: 4133
26 Ding X.-B, Wung A, Furkert DP, Brimble MA. Org. Biomol. Chem. 2023; 21: 6008
27 Freeman JL, Li FF, Furkert DP, Brimble MA. Synlett 2020; 31: 657
28 Freeman JL, Brimble MA, Furkert DP. Org. Biomol. Chem. 2019; 17: 2705
29 Wang Z, Krogsgaard-Larsen N, Daniels B, Furkert DP, Brimble MA. J. Org. Chem. 2016; 81: 10366
30 Earl AD, Li FF, Ma C, Furkert DP, Brimble MA. Org. Biomol. Chem. 2023; 21: 1222
31 Fry DF, Fowler CB, Dieter RK. Synlett 1994; 836
32 Gallulo V, Dimas L, Zezza CA, Smith MB. Org. Prep. Proced. Int. 1989; 21: 297
33 Jost T, Heymann T, Glomb MA. J. Agric. Food Chem. 2019; 67: 3046

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