Tetrahedron letters

A reversible safety-catch method for the hydrogenolysis of N-benzyl moieties

DC Johnson, TS Widlanski

文献索引：Johnson II, David C.; Widlanski, Theodore S. Tetrahedron Letters, 2004 , vol. 45, # 46 p. 8483 - 8487

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被引用次数: 9

摘要

The benzyl groups of β-hydroxy-N-benzyl sulfonamides are labile toward hydrogenolysis- unlike N-benzyl sulfonamides lacking the β-hydroxy moiety. We find that N-acyl-N-benzyl sulfonamides undergo hydrogenolysis under very mild conditions. Based upon these observations, we developed a reversible safety-catch method using tert-butoxycarbonyl moieties to activate N-benzyl sulfonamides toward hydrogenolysis. We also explored the ...