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anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst.
J Am Chem Soc. 2005 Nov 30; 127(47):16408-9.JA

Abstract

A direct asymmetric Mannich reaction using a novel axially chiral amino trifluoromethanesulfonamide (S)-3 has been developed in highly anti-selective and enantioselective manners. Thus, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and the alpha-imino ester 4 proceed smoothly to give the functional beta-amino aldehydes with significantly higher anti/syn ratio and enantioselectivity than previously possible.

Authors+Show Affiliations

Kano T
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Yamaguchi Y
No affiliation info available
Tokuda O
No affiliation info available
Maruoka K
No affiliation info available

MeSH

AldehydesCatalysisHeterocyclic Compounds, 4 or More RingsMannich BasesMolecular StructureStereoisomerismSulfonamides

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16305223

Citation

Kano, Taichi, et al. "Anti-selective Direct Asymmetric Mannich Reactions Catalyzed By Axially Chiral Amino Sulfonamide as an Organocatalyst." Journal of the American Chemical Society, vol. 127, no. 47, 2005, pp. 16408-9.
Kano T, Yamaguchi Y, Tokuda O, et al. Anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst. J Am Chem Soc. 2005;127(47):16408-9.
Kano, T., Yamaguchi, Y., Tokuda, O., & Maruoka, K. (2005). Anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst. Journal of the American Chemical Society, 127(47), 16408-9.
Kano T, et al. Anti-selective Direct Asymmetric Mannich Reactions Catalyzed By Axially Chiral Amino Sulfonamide as an Organocatalyst. J Am Chem Soc. 2005 Nov 30;127(47):16408-9. PubMed PMID: 16305223.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst. AU - Kano,Taichi, AU - Yamaguchi,Yukako, AU - Tokuda,Osamu, AU - Maruoka,Keiji, PY - 2005/11/25/pubmed PY - 2006/3/11/medline PY - 2005/11/25/entrez SP - 16408 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 127 IS - 47 N2 - A direct asymmetric Mannich reaction using a novel axially chiral amino trifluoromethanesulfonamide (S)-3 has been developed in highly anti-selective and enantioselective manners. Thus, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and the alpha-imino ester 4 proceed smoothly to give the functional beta-amino aldehydes with significantly higher anti/syn ratio and enantioselectivity than previously possible. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16305223/anti_selective_direct_asymmetric_Mannich_reactions_catalyzed_by_axially_chiral_amino_sulfonamide_as_an_organocatalyst_ DB - PRIME DP - Unbound Medicine ER -