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COMMUNICATION
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When the migrating group is silyl (allylic silyl ether), the
DOI: 10.1039/C6CC04626F
rearrangement is called as a retro‐[1,4] Brook
rearrangement: (a) Z. Gan, Y. Wu, L. Gao, X. Sun, J. Lei, Z.
Song and L. Li, Tetrahedron, 2012, 68, 6928; (b) Z. Song, Z.
Lei, L. Gao, X. Wu and L. Li, Org. Lett., 2010, 12, 5298; (c) A.
Nakazaki, T. Nakai and K. Tomooka, Angew. Chem. Int. Ed.,
2006, 45, 2235.
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A review on aza‐Wittig rearrangement: C. Vogel, Synthesis,
1997, 497.
Recent examples of aza‐[2,3] and [1,2] Wittig
rearrangements: (a) R. K. Everett and J. P. Wolfe, J. Org.
Chem., 2015, 80, 9041; (b) B. Drouillat, K. Wright, P.
Quinodoz, J. Marrot and F. Couty, J. Org. Chem., 2015, 80
6936; (c) R. K. Everett and J. P. Wolfe, Tetrahedron Lett.,
2015, 56, 3393; (d) J. C. Anderson and E. A. Davies,
Tetrahedron, 2005, 66, 6300; (e) P. Tuzina and P. Somfai,
,
Org. Lett., 2009, 11, 919; (f) J. Blid, O. Panknin, P. Tuzina and
P. Somfai, J. Org. Chem., 2007, 72, 1294; (g) P. Somfai and O.
Panknin, Synlett, 2007, 1190; (h) P. Tuzina and P. Somfai,
Tetrahedron Lett., 2007, 48, 4947.
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This ammonium ylide rearrangement may be referred to as a
[1,4] Stevens rearrangement: (a) R. W. Jemison, T. Laird, W.
D. Ollis and I. O. Sutherland, J. Chem. Soc., Perkin Trans. 1,
1980, 1436; (b) H. Felkin and C. Frajerman, Tetrahedron Lett.,
1977, 18, 3485; (c) R. K. Hill and T.‐H. Chan, J. Am. Chem.
Soc., 1966, 88, 866; (d) H. Hellmann and G. M. Scheytt,
Liebigs Ann. Chem., 1962, 654, 39; (e) E. F. Jenny and J.
Druey, Angew. Chem. Int. Ed., 1962, 1, 155; (f) H. Hellmann
and G. M. Scheytt, Liebigs Ann. Chem., 1961, 642, 22.
Previous examples of base‐promoted (anionic)
rearrangement of hydrazine derivatives involving an N–N
bond cleavage: (a) Y. Gong, M. J. Bausch and L. Wang,
Tetrahedron Lett., 2001, 42, 1; (b) Y. Endo, T. Uchida and K.
Yamaguchi, Heterocycles, 2000, 53, 151; (c) Y. Endo, T.
Uchida and K. Shudo, Tetrahedron Lett., 1997, 38, 2113; (d)
C. von Rohrscheidt and H. Fritz, Liebig Ann. Chem., 1978,
680.
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Representative examples of the preparation of ‐amino
enamides: (a) N. Gigant and I. Gillaizeau, Org. Lett., 2012, 14
4622; (b) A. W. Hill, M. R. J. Elsegood and M. C. Kimber, J.
Org. Chem., 2010, 75, 5406; (c) M. C. Kimber, Org. Lett.,
2010, 12, 1128.
,
(a) A. Bredihhin and U. Mäeorg, Tetrahedron, 2008, 64, 6788;
(b) A. Bredihhin and U. Mäeorg, Org. Lett., 2007, 9, 4975; (c)
A. Bredihhin, U. M. Groth and U. Mäeorg, Org. Lett., 2007, 9,
1097.
10 The stereochemistry of E‐ and Z‐10d were determined by
comparison of NOESY spectra. For details, see ESI.
11 Such a reaction via stepwise process may be referred to as a
Wittig‐type rearrangement. Selected examples: (a) K.
Uneyama, H. Ohkura, J. Hao and H. Amii, J. Org. Chem., 2001,
66, 1026; (b) C. S. B. Chia, M. S. Taylor, S. Dua, S. J. Blanksby
and J. H. Bowie, J. Chem. Soc., Perkin Trans. 2, 1998, 1435; (c)
A. Miyashita, Y. Matsuoka, Y. Suzuki, K. Iwamoto and T.
Higashino, Chem. Pharm. Bull., 1997, 45, 1235.
12 We also examined a reaction of tert‐butyl 1,2,2‐
triallylhydrazinecarboxylate to clarify the possibility of N,N‐
dialkylamino migrating group. However, the desired
products were not obtained.
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