- INTRODUCTION OF gem-DIALKYL GROUP TO HEXOFURANOSE BY ORTHO ESTER CLAISEN REARRANGEMENT
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The ortho ester Claisen rearrangement of D-ribo- or L-lyxo-hexofuranose derivative which possesses an allyl alcohol functionality on C-3, proceeds stereoselectively to give a 3-C-dialkylated product.The stereochemistry of a newly introduced quaternary center of the product was unambiguously established by a chemical modification.
- Tadano, Kin-Ichi,Idogaki, Yoko,Yamada, Hirohiko,Suami, Tetsuo
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- Ortho Ester Claisen Rearrangements of Three 3-C-(Hydroxymethyl)methylene Derivatives of Hexofuranose: Stereoselective Introduction of a Quaternary Center on C-3 of D-ribo-, L-lyxo-, and D-arabino-Hexofuranoses
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Ortho ester Claisen rearrangements of (E)-3-deoxy-3-C--1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose (3-E), -β-L-lyxo-hexafuranose (12-E), and -β-D-arabino-hexofuranose (33-E) proceeded with high stereoselectivity to provide the rearranged products 13, 15, and 34, respectively, in acceptable yields.The rearrangements of the corresponding Z isomers 3-Z, 12-Z, and 33-Z were also investigated.The stereochemistries of the newly introduced quaternary center on C-3 of compounds 13, 15, and 34 were established unambiguouosly by chemical modifications of each rearranged product.
- Tadano, Kin-ichi,Idogaki, Yoko,Yamada, Hirohiko,Suami, Tetsuo
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p. 1201 - 1210
(2007/10/02)
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