Citation: Jia Shi-Kun, Lei Yu-Bing, Song Long-Long, Liu Shun-Ying, Hu Wen-Hao. Enantioselective trapping of oxonium ylide intermediates by N-benzhydryl-α-imino ester: Synthesis of β-tetrasubstituted α-amino acids[J]. Chinese Chemical Letters, ;2017, 28(2): 213-217. doi: 10.1016/j.cclet.2016.06.053 shu

Enantioselective trapping of oxonium ylide intermediates by N-benzhydryl-α-imino ester: Synthesis of β-tetrasubstituted α-amino acids

Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Chemical Engineering, East China Normal University, Shanghai 200062, China

Corresponding author: Liu Shun-Ying, syliu@sist.ecnu.edu.cn Hu Wen-Hao, whu@chem.ecnu.edu.cn
Received Date: 12 May 2016
Revised Date: 15 June 2016
Accepted Date: 24 June 2016
Available Online: 25 February 2016

Figures(5)

A synergistic rhodium(II)/phosphoric acid catalyzed three component reaction of 3-diazooxindoles, alcohols and N-benzhydryl-α-imino ester is developed for the efficient construction of chiral β-alkoxy C^β-tetrasubstituted α-amino acid derivatives in good yields and with excellent diastereoselectivities and high enantioselectivities. The synthetic application of the resulting products was illustrated by reducing with Pd/C under H₂ atmosphere followed reacting with CSCl₂ at room temperature to rapid afford 3-spirocyclic oxindole in a good yield with a chirality retainment. The three-component reaction is proposed to proceed through an electrophilic trapping of the oxonium ylides by N-benzhydryl-α-imino ester.
- Three-component reaction,
- Oxonium ylide,
- N-Benzhydryl-α-imino ester,
- β-Tetrasubstituted α-amino acids,
- Chiral phosphoric acid
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