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Synlett 1999; 1999(2): 213-215
DOI: 10.1055/s-1999-2577
DOI: 10.1055/s-1999-2577
letter
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Diastereoselective Synthesis of Methylated α-Methoxy-8-oxabicyclo[3.2.1]oct-6-en-3-ones. Contrathermodynamic Introduction of Methoxy Group by Low Temperature [4 + 3]-Cycloaddition
Further Information
Publication History
Publication Date:
31 December 1999 (online)
A series of α,α-dimethoxysilyl enol ethers has been prepared and shown to undergo diastereoselective [4 + 3]-cycloaddition with furan and cyclopentadiene in the presence of catalytic trimethylsilyl triflate. The α-methoxy group of the resulting title oxabicyclics preferentially adopts the contrathermodynamic equatorial position.
α,α-dimethoxysilyl enol ethers - methoxy-2-silyloxyallyl cation intermediates - silicon bridging - kinetic control - dictyoxetane models