TY - JOUR A1 - Uno, Takuya A1 - Kobayashi, Yusuke A1 - Takemoto, Yoshiji T1 - N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters JF - Beilstein Journal of Organic Chemistry PY - 2012/// VL - 8 SP - 1499 EP - 1504 SN - 1860-5397 DO - 10.3762/bjoc.8.169 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.8.169 KW - α-amino-β-keto esters KW - cross-aza-benzoin KW - α-imino ester KW - N-heterocyclic carbenes KW - organocatalysis KW - umpolung reactions N2 - 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. ER -