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29744462763
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Extensive work on different propargylic alcohols led to a general protocol for the preparation of aromatic and heteroaromatic sulfones as reported in: Bonini, C.; Chiummiento, L.; Videtta, V. Synlett 2005, 3067.
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33749360095
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note
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The stereochemical outcome of the one-pot Julia olefination is generally substrate (sulfone and aldehyde) controlled. Moreover, there are some examples where β,γ-unsaturated BT-sulfones give high levels of E stereoselectivity (see ref. 7a).
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32
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0037463727
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Bonini, C.; Chiummiento, L.; Lopardo, M. T.; Pullez, M.; Colobert, F.; Solladié, G. Tetrahedron Lett. 2003, 44, 2695.
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Bonini, C.1
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Lopardo, M.T.3
Pullez, M.4
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Solladié, G.6
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33
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22744448499
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For recent reviews of the alkene metathesis reaction, see: (a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4490.
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Nicolaou, K.C.1
Bulger, P.G.2
Sarlah, D.3
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37
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33748276427
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These high Z selectivities prompted us to study the one-pot Julia olefination with propargylic sulfone 6 and several different aromatic and aliphatic aldehydes more extensively: Bonini, C.; Chiummiento, L.; Videtta, V. Synlett 2006, 2079.
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(2006)
Synlett
, pp. 2079
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Bonini, C.1
Chiummiento, L.2
Videtta, V.3
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40
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33749315914
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note
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Attempts were made to prepare the tributyl propargylic phosphorane but we had some problems obtaining it pure.
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41
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33749340113
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note
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2: C, 64.23; H, 9.24. Found: C, 64.32; H, 9.18.
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