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ortho ‐Anisylsulfonyl as a Protecting Group for Secondary Amines: Mild Ni 0 ‐Catalyzed Hydrodesulfonylation
Author(s) -
Milburn Robert R.,
Snieckus Victor
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352634
Subject(s) - alkylation , primary (astronomy) , catalysis , chemistry , group (periodic table) , tosyl , medicinal chemistry , combinatorial chemistry , organic chemistry , physics , astronomy
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, Ni 0 ‐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.