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Synfacts 2006(1): 0074-0074
DOI: 10.1055/s-2005-921709
DOI: 10.1055/s-2005-921709
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York
Organocatalytic anti-Selective Direct Mannich Reaction
T. Kano, Y. Yamaguchi, O. Tokuda, K. Maruoka*
Kyoto University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
16. Dezember 2005 (online)
Significance
Several aldehydes (1) and α-amino esters (2) were transformed to the corresponding β-amino aldehydes in an anti-selective manner by using chiral amino sulfonamides (3) in low catalyst loadings (2 mol%). It turned out that the presence of the trifluoromethyl group on the sulfonamide moiety was necessary to achieve good yields as well as good anti/syn ratios and nearly complete enantioselectivity. For more sterically hindered aldehydes (e.g., R1 = i-Pr) higher catalyst loading (5 mol%) was required. No self-aldolization products were formed.