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Synfacts 2017; 13(11): 1180
DOI: 10.1055/s-0036-1591337
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of γ-Amino Esters by Palladium-Catalyzed Allylic Amination

Contributor(s):
Hisashi Yamamoto
,
Tomohiro Hattori
Xia C. Shen J. Liu D. * Zhang W. * Shanghai Jiao Tong University, P. R. of China
Synthesis of Chiral α,β-Unsaturated γ-Amino Esters via Pd-Catalyzed Asymmetric Allylic Amination.

Org. Lett. 2017;
19: 4251-4254
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Publication History

Publication Date:
19 October 2017 (online)

 
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Key words

aminoalkenoate esters - allylic amination - palladium catalysis - acetoxybutenoates

Significance

Chiral α,β-unsaturated γ-amino esters are ubiquitous in various chemical and biological fields. The authors describe a direct catalytic asymmetric synthesis of chiral α,β-unsaturated γ-amino esters from 2-acetoxybut-3-enoates and amines.


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Comment

Pd-catalyzed asymmetric allylic amination of 4-substituted 2-acetoxybut-3-enoates with various amines proceeds smoothly to give chiral α,β-unsaturated γ-amino esters in excellent yields and high enantioselectivities.


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