4.7 Article

Michael addition of amines and thiols to dehydroalanine amides: A remarkable rate acceleration in water

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 26, Pages 10098-10102

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo034762z

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In water, the rate of Michael addition of amines and thiols to dehydroalanine amides was greatly accelerated, leading to shorter reaction times and higher yields. The scope of the new conditions was tested with a range of amines, thiols, and dehydroalanine amides. The ease and efficiency of this method provides an attractive route to the synthesis of natural and unnatural amino acid derivatives.

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