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New Trialkylsilyl Enol Ether Chemistry: α-N-Tosylamination of Triisopropylsilyl Enol Ethers
Magnus, Philip,Lacour, Jerome,Coldham, Iain,Mugrage, Benjamin,Bauta, William B.
, p. 11087 - 11110 (2007/10/02)
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 azabicyclononane skeleton, the core structure of a number of alkaloids.
