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A potentially good alternative to the tosyl group (Ts) as a protecting group for amines is N-ortho-anisylsulfonyl (Ans), which is readily cleaved under mild, Ni0-catalyzed reductive conditions (see scheme, acac=acetylacetonate). N-Anisylation of primary amines followed by alkylation and deprotection provides a route to a range of secondary amines.
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Milburn et al. (2004) studied this question.
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