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and the secondary boronic esters were prepared by the lithiation-borylation reaction of primary carabamates
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The tertiary boronic esters were prepared by the lithiation-borylation reaction of a secondary carbamate c) J. L. Stymiest, V. Bagutski, R. M. French, V. K. Aggarwal, Nature 2008, 456, 778, and the secondary boronic esters were prepared by the lithiation-borylation reaction of primary carabamates
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Oxidation of the 3:1 mixture of isomers gave a 3:1 mixture of ketones indicating that the diastereomeric mixture was due to E and Z alkene isomers. NOE studies confirmed the ZIE products
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Oxidation of the 3:1 mixture of isomers gave a 3:1 mixture of ketones indicating that the diastereomeric mixture was due to E and Z alkene isomers. NOE studies confirmed the ZIE products.
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77955889694
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X-ray analyses were achieved on the major enantiomer of the (Z)-p-nitrobenzaldehyde adduct and the major and minor enantiomers of the £ benzaldehyde adducts which were more readily separable. See the Supporting Information
-
X-ray analyses were achieved on the major enantiomer of the (Z)-p-nitrobenzaldehyde adduct and the major and minor enantiomers of the £ benzaldehyde adducts which were more readily separable. See the Supporting Information.
-
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-
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46
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0001055223
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A similar reactivity through an open TS was invoked in the reactions of lithium allylic borate complexes with aldehydes. See: Y. Yamamoto, H. Yalagai, K. Maruyama, J. Am. Chem. Soc. 1981, 103, 1969.
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A primary 4-methoxybenzyl Grignard reagent has also been reported to react with certain aldehydes through the aromatic ring with concomitant dearomatisation. See: a) G. A. Kraus, I. Kim, S. Kesavan, Tetrahedron Lett. 2004, 45, 6839
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77955889038
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For Pd-catalysed allylative dearomatisation of benzylic chlorides see reference [3i]
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b) For Pd-catalysed allylative dearomatisation of benzylic chlorides see reference [3i]
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49
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0036183602
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2 through the aromatic ring followed by rapid rearomalisation. See: J. G. Peters, M. Seppi, R. Fröhlich, B. Wibbeling, D. Hoppe, Synthesis 2002, 381.
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77955879153
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The primary p-methoxybenzyl trifluoroborate salt was also tested and gave the corresponding homoallylic alcohol related to 2 in 36% yield (unoptimized). See the Supporting Information for details
-
The primary p-methoxybenzyl trifluoroborate salt was also tested and gave the corresponding homoallylic alcohol related to 2 in 36% yield (unoptimized). See the Supporting Information for details.
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