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The known piperidone was prepared in five steps and 35% overall yield from 4-methoxyphenylmethylhex-5-enoate; see: Hodgkinson, T. J.; Shipman, M. Synthesis 1998, 1141.
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Hodgkinson, T.J.1
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9
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37049074279
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(c) Fujii, N.; Nakai, K.; Tamamura, H.; Otaka, A.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1995, 1359.
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14
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(b) Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S. Tetrahedron 1990, 46, 3667. Aldehyde (-)-10 was prepared in four steps and 95% overall yield from commercially available ethyl (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-propenoate (i): see the Supporting Information for details.
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Chattopadhyay, S.1
Mamdapur, V.R.2
Chadha, M.S.3
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20
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23044509792
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note
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In this case, use of HMPA or DMPU as cosolvents to trigger the Brook rearrangement resulted in poor yield (<10%).
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21
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0035813419
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(a) Okada, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 8023.
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0035813444
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(b) Arisawa, M.; Theeraladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029.
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Arisawa, M.1
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23
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0033598258
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25
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0027173923
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(b) Barton, D. H. R.; Parekh, S. I.; Tse, C.-L. Tetahedron Lett. 1993, 34, 2733.
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Barton, D.H.R.1
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Tse, C.-L.3
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27
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23044452702
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note
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Hydrolysis at room temperature for 12 h led to a mixture (ca. 1:1) of aldehydes.
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28
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23044451933
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see ref 3
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The stereochemistry at the newly formed position in (+)-16 was later confirmed by comparison of the NMR data of (-)-19 with those of known (+)-19; see ref 3.
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29
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0035929396
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(a) Fleming, F. F.; Funk, L.; Altundas, R.; Tu, Y. J. Org. Chem. 2001, 66, 6502.
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