New Trialkylsilyl Enol Ether Chemistry: α-N-Tosylamination of Triisopropylsilyl Enol Ethers

Article abstract of DOI:10.1016/0040-4020(95)00696-6

Triisopropylsilyl enol ethers react with (TsN)2Se to give α-N-tosylamino derivatives in modest to good yields.In the absence of 1,3-diaxial interactions the N-tosylamino group prefers an axial conformation.The axial N-tosylamino derivatives can be readily transformed into the azabicyclo<3.3.1>nonane skeleton, the core structure of a number of alkaloids.