-
2
-
-
33645332652
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-
note
-
2Et resulted in the formation of an O-carbamoyl derivative.
-
-
-
-
3
-
-
0001622693
-
-
For discussions on stereochemistry in the reactions in which enol silyl ethers are formed from α-silyl alkoxides bearing a β-leaving group via the Brook rearrangement, see: H.J. Reich, R.C. Holtan, and C. Bolm J. Am. Chem. Soc. 112 1990 5609 5617
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(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 5609-5617
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-
Reich, H.J.1
Holtan, R.C.2
Bolm, C.3
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6
-
-
33645349088
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-
note
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To the best of our knowledge, there is no precedent for a stereochemical discussion concerning Brook rearrangement in α-silyl allylalkoxides.
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-
-
-
10
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-
0035835953
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-
For the use of the Brook rearrangement in tandem bond formation strategies, see: W.H. Moser Tetrahedron 57 2001 2065 2084
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(2001)
Tetrahedron
, vol.57
, pp. 2065-2084
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-
Moser, W.H.1
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16
-
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33645336863
-
-
note
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3; Z = 4; R = 0.0702.
-
-
-
-
17
-
-
0000152732
-
-
To the best of our knowledge, this is the first X-ray crystal structure of α-trialkylsilyl allylic alcohol. For an X-ray structure of (1-hydroxyprop-2-eny1)silanol, see: J.D. Buynak, J.B. Strickland, G.W. Lamb, D. Khasnis, S. Modi, D. Williams, and H. Zhang J. Org. Chem. 56 1991 7076 7083
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(1991)
J. Org. Chem.
, vol.56
, pp. 7076-7083
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-
Buynak, J.D.1
Strickland, J.B.2
Lamb, G.W.3
Khasnis, D.4
Modi, S.5
Williams, D.6
Zhang, H.7
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18
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-
0000024039
-
Hypervalent Silicon Compounds
-
Z. Rappoport Y. Apeloig Wiley Chichester, UK
-
For reviews of hypervalent silicon compounds, see: D. Kost, and I. Kalikhman Hypervalent Silicon Compounds Z. Rappoport Y. Apeloig The Chemistry of Organic Silicon Compounds Vol. 2 1998 Wiley Chichester, UK Chapter 23
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(1998)
The Chemistry of Organic Silicon Compounds
, vol.2
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-
Kost, D.1
Kalikhman, I.2
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20
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0037148833
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-
S. Deerenberg, M. Schakel, A.H.J.F. de Keijzer, M. Kranenburg, M. Lutz, A.L. Spek, and K. Lammertsma Chem. Commun. 2002 348 349 Also, see: Ref. 5a
-
(2002)
Chem. Commun.
, pp. 348-349
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-
Deerenberg, S.1
Schakel, M.2
De Keijzer, A.H.J.F.3
Kranenburg, M.4
Lutz, M.5
Spek, A.L.6
Lammertsma, K.7
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27
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-
0344391973
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-
We have previously reported the possibility that C-O bond cleavage and Si-O bond formation in base-promoted ring opening of metalated O-silyl cyanohydrins of β-silyl-α,β-epoxyaldehydes proceed in a concerted manner. See: M. Sasaki, E. Kawanishi, E. Nakai, T. Matsumoto, K. Yamaguchi, and K. Takeda J. Org. Chem. 68 2003 9330 9339
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(2003)
J. Org. Chem.
, vol.68
, pp. 9330-9339
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Sasaki, M.1
Kawanishi, E.2
Nakai, E.3
Matsumoto, T.4
Yamaguchi, K.5
Takeda, K.6
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32
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-
33645377560
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-
note
-
Treatment of 3 with KHMDS (1.1 equiv) in the presence of MeI and 18-crown-6 (0.05 equiv) in THF at 0°C for 5 min, conditions that roughly mimic those which can be encountered in the reaction from 1a, resulted in the formation of 4 (52% yield; E/Z = 1/2.5) and protonated derivative 2 (El = H) (28% yield; E/Z = 1/6.7).
-
-
-
-
33
-
-
33645336585
-
-
note
-
2Et provided (5E)-10a in 93% yield. See Ref. 1.
-
-
-
-
34
-
-
33645338482
-
-
note
-
The use of less bulky silyl groups such as trimethylsilyl and dimethylphenylsilyl resulted in the hydrolysis of the enol silyl ether to the corresponding aldehydes.
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