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N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of ?-amino-?-keto esters.

ABSTRACT: An efficient catalytic synthesis of ?-amino-?-keto esters has been newly developed. Cross-coupling of various aldehydes with ?-imino ester, catalyzed by N-heterocyclic carbene, leads chemoselectively to ?-amino-?-keto esters in moderate to good yields with high atom efficiency. The reaction mechanism is discussed, and it is proposed that the ?-amino-?-keto esters are formed under thermodynamic control.

SUBMITTER: Uno T 

PROVIDER: S-EPMC3458774 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters.

Uno Takuya T   Kobayashi Yusuke Y   Takemoto Yoshiji Y  

Beilstein journal of organic chemistry 20120910

An efficient catalytic synthesis of α-amino-β-keto esters has been newly developed. Cross-coupling of various aldehydes with α-imino ester, catalyzed by N-heterocyclic carbene, leads chemoselectively to α-amino-β-keto esters in moderate to good yields with high atom efficiency. The reaction mechanism is discussed, and it is proposed that the α-amino-β-keto esters are formed under thermodynamic control. ...[more]

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