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Synfacts 2010(2): 0187-0187  
DOI: 10.1055/s-0029-1219091
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Sc(III)-Catalyzed Direct Aldol Reaction of α-Keto Esters with Diazoacetate Esters

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
F. Wang, X. Liu, Y. Zhang, L. Lin, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publikationsdatum:
21. Januar 2010 (online)

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Significance

The authors have developed a C 2-symmetric N,N′-dioxide-Sc(III) complex for the asymmetric direct aldol reaction of α-keto esters with diazoacetates. Aromatic and heteroaromatic α-keto esters provided the desired tertiary alcohols in good yields and excellent enantioselectivities. The desired product was converted into the known compound via hydrogenation to determine the absolute configuration without any loss of enantioselectivity.