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Synfacts 2014; 10(5): 0509
DOI: 10.1055/s-0033-1341175
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Ruthenium-Catalyzed Asymmetric Allylic Amination

Contributor(s):
Mark Lautens
,
Zafar Qureshi
Kawatsura M, * Uchida K, Terasaki S, Tsuji H, Minakawa M, Itoh T. * Nihon University, Tokyo and Tottori University, Japan
Ruthenium-Catalyzed Regio- and Enantioselective Allylic Amination of Racemic 1-Arylallyl Esters.

Org. Lett. 2014;
16: 1470-1473
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Publication History

Publication Date:
17 April 2014 (online)

 
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Key words

ruthenium - allylic amination - pybox ligand

Significance

The asymmetric transition-metal-catalyzed allylic amination has proven to be an indispensable tool for synthetic chemists for synthesizing branched amines. The first example of asymmetric allylic amination of mono-substituted allylic substrates was reported by T. Hayashi et al. (Tetrahedron Lett. 1990, 31, 1743). The authors here report the ruthenium-catalyzed enantioselective allylic amination of racemic monosubstituted allylic esters with cyclic and acyclic secondary amines.


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Comment

Although the reaction was amenable to a variety of aromatic groups, bulky ortho substituents were not well tolerated. Both cyclic and acyclic secondary amines gave good yields and enantioselectivities. Substrates where the aromatic group was replaced by an alkyl group were not explored or reported.


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