Reversal of enantioselectivity by adding Ti(OiPr)4: Novel sulfamide-amine alcohol ligands for the catalytic asymmetric addition of diethylzinc to aldehydes

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Abstract

Novel sulfamide-amine alcohols (6) were applied to the catalytic asymmetric addition of diethylzinc to aldehydes, providing (S)-products in high yields and good enantioselectivities. These sulfamide-amie alcohols together with Ti(OiPr)4were shown to obtain the (R)-products in significant enantiomeric excesses and high yields. Novel sulfamide-amine alcohol ligands (6) derived from (-)-ephedrine (4a) and (+)-pseudoephedrine (4b) with multiple stereogenic centers were applied to the catalytic asymmetric addition of diethylzinc to aldehydes, providing (S)-products in high yields and good enantioselectivities. These sulfamide-amine alcohols together with Ti(OiPr)4were shown to obtain the (R)-products in significant enantiomeric excesses (e.e.) and high yields. In addition, sulfamide-amine alcohols were superior to the original chiral sources 4a and 4b, which afforded no enantioselectivity in the Ti(OiPr)4-mediated reaction. © 2004 Elsevier B.V. All rights reserved.

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Mao, J., Wan, B., Zhang, Z., Wang, R., Wu, F., & Lu, S. (2005). Reversal of enantioselectivity by adding Ti(OiPr)4: Novel sulfamide-amine alcohol ligands for the catalytic asymmetric addition of diethylzinc to aldehydes. Journal of Molecular Catalysis A: Chemical, 225(1), 33–37. https://doi.org/10.1016/j.molcata.2004.08.027

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