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note
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III]OAc (2 mol %) to give the desired chiral epoxyketal in 50 % overall yield (95 % ee). Lower yields may be attributed to epoxide opening by MeOH during the ketalization step with higher catalyst loadings of the monomeric catalyst. See the Supporting Information for details.
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40
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33845796600
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note
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The diastereomer which corresponds to racemization of the allylic center was independently synthesized and was not detected in the HPLC analysis of the products (see the Supporting Information for details).
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(see the Supporting Information for details)
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The silyl groups were removed and (-)-11 was peracetylated to give 1,2,3,6-O-tetraacetyl-4-O-benzyl-L-galactopyranose, the spectroscopic data of which was found to correspond to those reported for the known compound (see the Supporting Information for details): L. Ermolenko, N. A. Sasaki, J. Org. Chem. 2006, 71, 693.
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