The Journal of Organic Chemistry

Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure-Reactivity Studies and Use of the 2-(tert- …

LA Carpino, M Philbin

Index: Carpino, Louis A.; Philbin, Michael Journal of Organic Chemistry, 1999 , vol. 64, # 12 p. 4315 - 4323

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Citation Number: 26

Abstract

A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael acceptors showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2> Me3CSO2> COOEt> C6H5SO> C6H4NO2-p. The reactivity of the nucleophile (eg, primary and secondary aliphatic amines) followed an ...

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Amino-Protecting Groups Subject to Deblocking under Conditio...

[Journal of Organic Chemistry, , vol. 64, # 12 p. 4315 - 4323]