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- W2103209804 abstract "The (E)- and (Z)-terpene-based aldehydes 6b and 6c with a silyl ether function in the γ-position were prepared and investigated in boron-mediated asymmetric Evans aldol reactions. Screening experiments of chiral N-acylated oxazolidinones 7, which are conveniently accessible from 5-methyl-5-hexenoic acid and Evans oxazolidinone auxiliaries, with various boron triflates and terpenoid neral (Z)-6a as aldehyde component, provided conditions in which highly selective formation of syn-aldol adduct 5a occurred and competing C=C double bond isomerization to 10 was completely suppressed. Applying the optimized conditions to O-silylated aldehydes 6b and 6c and N-acyloxazolidinone derivative (R)-7a confirmed the syn-selectivity and gave the appropriate products syn-5b,c and syn-21b,c in good yields. In the case of neral-derived syn adduct 5a, the configuration of the new stereogenic centers C-2/C-3 could be assigned as (2R,3S)." @default.
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- W2103209804 date "2014-09-04" @default.
- W2103209804 modified "2023-10-16" @default.
- W2103209804 title "Asymmetric Evans<i>syn</i>-Aldol Reactions of Terpene-Derived Enals: Scope and Limitations" @default.
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- W2103209804 doi "https://doi.org/10.1002/ejoc.201402736" @default.
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