10.1002/anie.201907060
Angewandte Chemie International Edition
COMMUNICATION
R. Frei, F. Benfatti, E. Serrano, J. Waser, Chem. Commun. 2014, 50,
10912; d) V. A. Rassadin, Y. Six, Tetrahedron 2016, 72, 4701.
[7]
Selected reviews on Hofmann–Löffler–Freytag reaction, see: a) M. E.
Wolff, Chem. Rev. 1963, 63, 55; b) R. S. Neale, Synthesis 1971, 1971,
1; c) L. Stella, Angew. Chem. Int. Ed. 1983, 22, 337; Angew. Chem. 1983,
95, 368; d) J. L. Jeffrey, R. Sarpong, Chem. Sci. 2013, 4, 4092. For
selected examples of recent progress on the Hofmann–Löffler–Freytag
reaction, see: e) C. Martinez, K. Muniz, Angew. Chem. Int. Ed. 2015, 54,
8287; Angew. Chem. 2015, 127, 8405; f) C. Q. O’Broin, P. Fernandez,
C. Martínez, K. Muniz, Org. Lett. 2016, 18, 436; g) P. Becker, T. Duhamel,
C. J. Stein, M. Reiher, K. Muꢀiz, Angew. Chem. Int. Ed. 2017, 56, 8004;
Angew. Chem. 2017, 129, 8117; h) T. Duhamel, C. J. Stein, M. Reiher,
K. Muꢀiz, ACS Catal. 2018, 8, 3918; i) P. Becker, T. Duhamel, C.
Martínez, K. Muꢀiz, Angew. Chem. Int. Ed. 2018, 57, 5166; Angew.
Chem. 2018, 130, 5262; j) Qin, Q.; Yu, S. Org. Lett. 2015, 17, 1894; k)
N. R. Paz, D. Rodríguez-Sosa, H. Valdes, R. Marticorena, D. Melian, M.
B. Copano, C. C. Gonzalez, A. Herrera, J. Org. Lett. 2015, 17, 2370; l)
E. A. Wappes, S. C. Fosu, T. C. Chopko, D. A. Nagib, Angew. Chem. Int.
Ed. 2016, 55, 9974; Angew. Chem. 2016, 128, 10128; m) E. A. Wappes,
K. M. Nakafuku, D. A. Nagib, J. Am. Chem. Soc. 2017, 139, 10204; n) J.
Long, X. Cao, L. Zhu, R. Qiu, C.-T. Au, S.-F. Yin, T. Iwasaki, N. Kambe,
Org. Lett. 2017, 19, 2793; o) D. Zhang, H. Wang, H. Cheng, J. G.
Hernandez, C. Bolm, Adv. Synth. Catal. 2017, 359, 4274; p) X.-Q. Mou,
X.-Y.Chen, G. Chen, G. He, Chem. Commun. 2018, 54, 515; q) D. Chang,
R. Zhao, C. Wei, Y. Yao, Y. Liu, L. Shi, J. Org. Chem. 2018, 83, 3305.
[2]
a) N. M. Aston, P. Bamborough, J. B. Buckton, C. D. Edwards, D. S.
Holmes, K. L. Jones, V. K. Patel, P. A. Smee, D. O. Somers, G. Vitulli, A.
L. Walker, J. Med. Chem. 2009, 52, 6257; b) T. Malcomson, K. Yelekci,
M. T. Borrello, A. Ganesan, E. Semina, N. De Kimpe, S. Mangelinckx, R.
R. Ramsay, FEBS Journal. 2015, 282, 3190; c) Y. Zheng, B. Liu, Z. Gou,
Y. Li, X. Zhang, Y. Wang, S. Yu, Y. Li, D. Sun, Bioorg. Med. Chem. Lett.
2015, 25, 791; d) Q. Zheng, Z. Chen, H. Wan, S. Tang, Y. Ye, Y. Xu, L,
Jiang, J. Ding, M. Geng, M. Huang, Y. Huang, Bioorg. Med. Chem. Lett.
2018, 28, 3808;
[3]
a) F. de Nanteuil, J. Waser, Angew. Chem. Int. Ed. 2011, 50, 12075;
Angew. Chem. 2011, 123, 12281; b) F. Benfatti, F. de Nanteuil, J. Waser,
Org. Lett. 2012, 14, 386; c) F. Benfatti, F. de Nanteuil, J. Waser, Chem.
Eur. J. 2012, 18, 4844; d) F. de Nanteuil, J. Loup, J. Waser, Org. Lett.
2013, 15, 3738; e) F. de Nanteuil, E. Serrano, D. Perrotta, J. Waser, J.
Am. Chem. Soc. 2014, 136, 6239; f) S. Racine, F. de Nanteuil, E. Serrano,
J. Waser, Angew. Chem. Int. Ed. 2014, 53, 8484; Angew. Chem. 2014,
126, 8624 ; g) E. Serrano, F. de Nanteuil, J. Waser, Synlett 2014, 25,
2285; h) S. Racine, B, Hegedus, R. Scopelliti, J. Waser, Chem. Eur. J.
2016, 22, 11997; i) J. Preindl, S, Chakrabarty, J. Waser, Chem. Sci. 2017,
8, 7112; j) D. Perrotta, M.-M. Wang, J. Waser, Angew. Chem. Int. Ed.
2018, 57, 5120; Angew. Chem. 2018, 130, 5214; k) A. R. Rivero, I.
Fernández, M. Á. Sierra, Org. Lett. 2013, 15, 4928; l) M. Zhu, D.-C. Wang,
M.-S. Xie, G.-R. Qu, H.-M. Guo, Chem. Eur. J. 2018, 24, 15512; m) E.-
R. Hao, D.-D. Fu, D.-C. Wang, T. Zhang, G.-R. Qu, G.-X. Li, Y. Lan, H.-
M. Guo, Org. Chem. Front., 2019, 6, 863; n) For a general review on DA
cyclopropanes, see: T. F. Schneider, J. Kaschel, D. B. Werz, Angew.
Chem., Int. Ed. 2014, 53, 5504.
[8]
[9]
E. E. J. Dekker, J. B. F. N. Engberts, Th. J. de. Boer, Recl. Trav. Chim.
Pays-Bas, 1978, 97, 39. In this work, only the aldehyde resulting from
hydrolysis of imines such as II could be isolated.
Similar dielectrophilic synthons can be obtained from acrolein by
condensation with an amine. However, they have not find widespread
use in organic synthesis due to their low stability and difficult synthesis.
See: M. Shimizu, I. Hachiya, I. Mizota, Chem. Commun. 2009, 874.
[4]
a) Y. Takemoto, S. Yamagata, S. Furuse, H. Hayase, T. Echigo, C. Iwata,
Chem. Commun. 1998, 651; b) J. D. Ha, J. Lee, S. C. Blackstock, J. K.
Cha, J. Org. Chem. 1998, 63, 8510; c) K. Wimalasena, H. B. Wickman,
M. P. D. Mahindaratne, Eur. J. Org. Chem. 2001, 3811; d) N. Ouhamou,
Y. Six, Org. Biomol. Chem. 2003, 1, 3007; e) C. Madelaine, Y. Six, O.
Buriez, Angew. Chem. Int. Ed. 2007, 46, 8046; Angew. Chem. 2007, 119,
8192; f) S. Maity, M. Zhu, R. S. Shinabery, N. Zheng, Angew. Chem. Int.
Ed. 2012, 51, 222; Angew. Chem. 2012, 124, 226; g) T. H. Nguyen, S.
Maity, N. Zheng, Beilstein J. Org. Chem. 2014, 10, 975.
[10] For selected reviews on transformations of imines and N,O-acetals, see:
a) S. Kobayashi, Y. Mori, J. S. Fossey, M. M. Salter, Chem. Rev. 2011,
111, 2626; b) Y.-Y. Huang, C. Cai, X. Yang, Z.-C. Lv, U. Schneider, ACS
Catal. 2016, 6, 5747.
[11] For a single example of oxidative ring-opening of a tosyl/alkyl-substituted
aminocyclopropane in the context of a total synthesis, see: N. C. Mancey,
N, Sandon, A.-L. Auvidet, R. J. Butlin, W, Czechtizky, J. P. A. Harrity,
Chem. Commun. 2011, 9804.
[5]
a) S. Rousseaux, B. Liégault, K. Fagnou, Chem. Sci. 2012, 3, 244; b) A.
Dos Santos, L. El Kaïm, L. Grimaud, R. Ramozzi, Synlett 2012, 438; c)
C. L. Ladd, D. S. Roman, A. B. Charette, Tetrahedron 2013, 69, 4479; d)
M. H. Shaw, E. Y. Melikhova, D. P. Kloer, W. G. Wittingham, J. F. Bower,
J. Am. Chem. Soc. 2013, 135, 4992; e) M. H. Shaw, N. G. McCreanor,
W. G. Wittingham, J. F. Bower, J. Am. Chem. Soc. 2015, 137, 463; f) M.
H. Shaw, R. A. Croft, W. G. Wittingham, J. F. Bower, J. Am. Chem. Soc.
2015, 137, 8054; g) M. H. Shaw, W. G. Wittingham, J. F. Bower,
Tetrahedron 2016, 72, 2731; h) N. G. McCreanor, S. Stanton, J. F. Bower,
J. Am. Chem. Soc. 2016, 138, 11465; i) G. W. Wang, J. F. Bower, J. Am.
Chem. Soc. 2018, 140, 2743; j) H. Kondo, K. Itami, J. Yamaguchi, Chem.
Sci. 2017, 8, 3799.
[12] D, A. Casteel, Nat. Prod. Rep. 1999, 16, 55.
[13] M. R. Faust, G. Hofner, J. Pabel, K. T. Wanner, Eur. J. Med. Chem. 2010,
45, 2453.
[14] a) G. Li, F. R. Fronczek, J. C. Antilla, J. Am. Chem. Soc. 2008, 130,
12216; b) W. Zheng, L. Wojtas, J. C. Antilla, Angew. Chem. Int. Ed. 2010,
49, 6589; Angew. Chem. 2010, 122, 6739; c) S. Nakamura, S. Takahashi,
Org. Lett. 2015, 17, 2590.
[15] For the ring-opening reaction, products involving C-C bond cleavage of
the more and less substituted C-C bonds were observed in a 1:1 ratio by
1H NMR of the crude reaction mixture. The iodides were too unstable to
be isolated in pure form. During the in situ SN2 reaction, the secondary
iodide decomposed and only 29 could be isolated. The observed 1:1 ratio
is surprising when considering the relative stability of secondary and
primary radicals, but may be due to a very early transition state
originating from high ring-strain.
[6]
To the best of our knowledge there is no report of a general synthesis of
1,3-difunctionalized
non-cyclic
propylamines
starting
from
aminocyclopropanes. For examples of the synthesis of 1,3-
difunctionalized propylamines starting from other types of cyclopropanes,
see: a) S. Das, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2017,
56, 11554; Angew. Chem. 2017, 129, 11712; b) S. M. Banik, K. M.
Mennie, E. N. Jacobsen, J. Am. Chem. Soc. 2017, 139, 9152; c) J.
Wallbaum, L. K. B. Garve, P. G. Jones, D. B. Werz, Org. Lett. 2017, 19,
98; d) D. B. Werz, A. U. Augustin, P. G. Jones, Chem. Eur. J. 2019, in
press, DOI: 10.1002/chem.201902160.
This article is protected by copyright. All rights reserved.