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1
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0003417469
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B. M. Trost and E. M. Fleming, Pergamon Press, New York, p. 1
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O. Mitsunobu, in Comprehensive Organic Synthesis, vol. 6, ed., B. M. Trost, and, E. M. Fleming, Pergamon Press, New York, 1991, p. 1
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Comprehensive Organic Synthesis, Vol. 6, Ed.
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Mitsunobu In, O.1
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8
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33750456293
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B. M. Trost, I. Fleming and L. A. Paquette, Pergamon Press, New York, p. 899; for a recent selected example, see:
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For a review, see: T. Hudlicky and J. W. Reed, in Comprehensive Organic Synthesis, vol. 5, ed., B. M. Trost, I. Fleming, and, L. A. Paquette, Pergamon Press, New York, 1991, p. 899
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Comprehensive Organic Synthesis, Vol. 5, Ed.
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Hudlicky, T.1
Reed In, J.W.2
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0003445429
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E. N. Jacobson, A. Pfaltz and H. Yamamoto, Springer-Verlag, Berlin, p. 621
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T. Katsuki, in Comprehensive Asymmetric Catalysis, vol. 2, ed., E. N. Jacobson, A. Pfaltz, and, H. Yamamoto, Springer-Verlag, Berlin, 1999, p. 621
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Comprehensive Asymmetric Catalysis, Vol. 2, Ed.
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Katsuki In, T.1
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13
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0037195680
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(a recent example) via the asymmetric dihydroxylation of alkenes, see:
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B. Olofsson P. Somfai J. Org. Chem. 2002 67 8574
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Olofsson, B.1
Somfai, P.2
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15
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0003445429
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E. N. Jacobson, A. Pfaltz and H. Yamamoto, Springer-Verlag, Berlin, p. 713 for the direct asymmetric epoxidation of conjugated dienes:
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I. E. Markó and J. S. Svendsen, in Comprehensive Asymmetric Catalysis, vol. 2, ed., E. N. Jacobson, A. Pfaltz, and, H. Yamamoto, Springer-Verlag, Berlin, 1999, p. 713
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(1999)
Comprehensive Asymmetric Catalysis, Vol. 2, Ed.
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Markó, I.E.1
Svendsen In, J.S.2
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0003445429
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E. N. Jacobson, A. Pfaltz and H. Yamamoto, Springer-Verlag, Berlin, p. 649
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E. N. Jacobson and M. H. Wu, in Comprehensive Asymmetric Catalysis, vol. 18, ed., E. N. Jacobson, A. Pfaltz, and, H. Yamamoto, Springer-Verlag, Berlin, 1999, p. 649
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(1999)
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Jacobson, E.N.1
Wu In, M.H.2
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22
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4143093678
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For ylide epoxidation starting from the pre-formed allylic sulfonium salt, see:
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V. K. Aggarwal C. L. Winn Acc. Chem. Res. 2004 37 611
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(2004)
Acc. Chem. Res.
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, pp. 611
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Aggarwal, V.K.1
Winn, C.L.2
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27
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0033537059
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For the alternative asymmetric synthesis of vinyl epoxides from addition of sulfonium ylide reagents to α,β-unsaturated aldehydes, see:
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A. Fürstner O. Guth A. Rumbo G. Seidel J. Am. Chem. Soc. 1999 121 11108
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J. Am. Chem. Soc.
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Fürstner, A.1
Guth, O.2
Rumbo, A.3
Seidel, G.4
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29
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33746909702
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see also ref. 113a and 14a
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see also ref. 113a and 14a
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-
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33
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33746921846
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see also ref. 10a for other rearrangement events; (e) see ref. 12 and 13 for further discussions
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see also ref. 10a for other rearrangement events; (e) see ref. 12 and 13 for further discussions.
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-
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35
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0041733341
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V. K. Aggarwal E. Alonso I. Bae G. Hynd K. M. Lydon M. J. Palmer M. Patel M. Porcelloni J. Richardson R. A. Stenson J. R. Studley J.-L. Vasse C. L. Winn J. Am. Chem. Soc. 2003 125 10926
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Aggarwal, V.K.1
Alonso, E.2
Bae, I.3
Hynd, G.4
Lydon, K.M.5
Palmer, M.J.6
Patel, M.7
Porcelloni, M.8
Richardson, J.9
Stenson, R.A.10
Studley, J.R.11
Vasse, J.-L.12
Winn, C.L.13
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36
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0042066450
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For an alternative asymmetric procedure making use of the pre-formation of the allylic sulfonium salt, see:
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K. Li X.-M. Deng Y. Tang Chem. Commun. 2003 2074
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(2003)
Chem. Commun.
, pp. 2074
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Li, K.1
Deng, X.-M.2
Tang, Y.3
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37
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0041853893
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For alternative approaches towards this motif, see:
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V. K. Aggarwal I. Bae H.-Y. Lee J. Richardson D. T. Williams Angew. Chem., Int. Ed. 2003 42 3274
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Angew. Chem., Int. Ed.
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Aggarwal, V.K.1
Bae, I.2
Lee, H.-Y.3
Richardson, J.4
Williams, D.T.5
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43
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0002793868
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and references cited therein To the best of our knowledge, this is the only precedent which supposes the in situ formation of these kind of epoxides (with a carboxylic acrylic acid moiety) from the addition of a sulfonium ylide to aldehydes. Unfortunately, this elegant process is poorly diastereoselective and cannot be catalytic in sulfide, see:
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K. Tanaka H. Horiuchi H. Yoda J. Org. Chem. 1989 54 63
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Tanaka, K.1
Horiuchi, H.2
Yoda, H.3
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51
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0026518702
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During this work, an elegant allylidenation of tosylimines to aziridines was described with 2-(bromomethyl)acrylate derivatives. However, these acrylates are β-functionalised with a phenyl group with could have an extra stabilisation effect of the alkene moiety:
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S. Nampalli R. S. Bhide H. Nakai Synth. Commun. 1992 22 1165
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(1992)
Synth. Commun.
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Nampalli, S.1
Bhide, R.S.2
Nakai, H.3
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