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- W2012093521 abstract "From our investigations on phosphine-catalyzed [4+2] annulations between α-alkyl allenoates and activated olefins for the synthesis of cyclohexenes, we discovered a hexamethylphosphorous triamide (HMPT)-catalyzed [4+2] reaction between α-alkyl allenoates 1 and arylidene malonates or arylidene cyanoacetates 2 that provides highly functionalized cyclohexenes 3 and 4 in synthetically useful yields (30-89%), with moderate to exclusive regioselectivity, and reasonable diastereoselectivity. Interestingly, the [4+2] annulations between the α-alkyl allenoates 1 and the olefins 2 manifested a polarity inversion of the 1,4-dipole synthon 1, depending on the structure of the olefin, thus providing cyclohexenes 3 exclusively when using arylidene cyanoacetates. The polarity inversion of α-alkyl allenoates from a 1,4-dipole A to B under phosphine catalysis can be explained by an equilibrium between the phosphonium dienolate C and the phosphorous ylide D." @default.
- W2012093521 created "2016-06-24" @default.
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- W2012093521 date "2011-07-07" @default.
- W2012093521 modified "2023-10-07" @default.
- W2012093521 title "Phosphine‐Catalyzed [4+2] Annulations of 2‐Alkylallenoates and Olefins: Synthesis of Multisubstituted Cyclohexenes" @default.
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- W2012093521 doi "https://doi.org/10.1002/asia.201100190" @default.
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