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0037033189
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For additional studies toward fragment synthesis, see: (a) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 185-187. (b) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 1593. (c) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 8883-8885.
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0037127487
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For additional studies toward fragment synthesis, see: (a) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 185-187. (b) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 1593. (c) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 8883-8885.
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For additional studies toward fragment synthesis, see: (a) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 185-187. (b) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 1593. (c) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 8883-8885.
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Negishi, E.1
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(b) For a related transformation, see: Jacobsen. E. N.; Chavez, D. E. Angew. Chem., Int. Ed. 2001, 40, 3667-3670.
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24
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4544367112
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note
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Pseudomonas AK lipase was purchased from Amano International Enzyme Co.
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25
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4544314430
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note
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The ee of recovered (S)-10 was >95%. See the Supporting Information for full characterization and the stereochemical assignments of 5 and 15.
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26
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0033525176
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For an example of lipase-mediated acryloyl transfer, see: Bisht, K. S.; Gross, R. A.; Kaplan, D. L. J. Org. Chem. 1999, 64, 780-789.
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0028846123
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White, J. D.; Bolton, D. L.; Dantanarayana, A. P.; Fox, C. M. J.; Hiner, R. N.; Jackson, R. W.; Sakuma, K.; Warrier, U. S. J. Am. Chem. Soc. 1995, 117, 1908-1939.
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33
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4544289952
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note
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Hydroxy aldehyde (21, R = H) displayed similar reactivity.
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35
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4544378757
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note
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Unusual reactivity of similar intermediates has been reported. See refs 4a,e,f and 5b for details.
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36
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0041350417
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For application in related ene-yne systems, see: Shi, J.; Zeng, X.; Negishi, E. Org. Lett. 2003, 5, 1825-1828.
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Shi, J.1
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0000906771
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For a discussion of electronic effects in Pd-mediated cross-couplings, see: Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
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Grushin, V.V.1
Alper, H.2
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39
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4544292928
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note
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Reproducibly, iodide 29 was recovered in 20-30% yield from this reaction. Attempts to increase iodide conversion to desired coupling product were unsuccessful.
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