Tetrahedron

New trialkylsilyl enol ether chemistry: α-N-tosylamination of triisopropylsilyl enol ethers

P Magnus, J Lacour, I Coldham, B Mugrage, WB Bauta

Index: Magnus, Philip; Lacour, Jerome; Coldham, Iain; Mugrage, Benjamin; Bauta, William B. Tetrahedron, 1995 , vol. 51, # 41 p. 11087 - 11110

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Citation Number: 60

Abstract

Triisopropylsilyl enol ethers reaet 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.