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- W2110184833 abstract "The enantiomerically pure alpha-methoxycarbaldehyde 3 was prepared from l-leucine in five steps and 31% overall yield. The aldehyde was subjected to a diastereoselective BF3-mediated crotylation with silane 4 and to various reagent-controlled addition reactions. The configuration of aldol addition products 19 and 20 was proven by single crystal X-ray crystallography. Based on these data spectral comparison allowed an unambiguous assignment of the desired anti,syn-crotylation product 2b and of the syn,syn-crotylation product 2a. Unexpectedly, product 2a of the BF3-mediated crotylation is formally the product of chelation-control. The anti,syn-crotylation product 2b, which is a model for the C-9/C-15 fragment of geldanamycin, was obtained by a reagent-controlled crotylation with the chiral (Z)-crotylborane 23." @default.
- W2110184833 created "2016-06-24" @default.
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- W2110184833 creator A5056881592 @default.
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- W2110184833 date "2006-09-15" @default.
- W2110184833 modified "2023-10-09" @default.
- W2110184833 title "Stereoselective allyl transfer to chiral α-methoxycarbaldehydes: A model study related to the C-9/C-15 fragment of geldanamycin" @default.
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- W2110184833 doi "https://doi.org/10.1016/j.bmc.2006.05.056" @default.
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