A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric anti-selective Mannich reactions and syn-selective cross-aldol reactions.
Chemistry. 2009 Jul 06; 15(27):6678-87.C

Abstract

A direct asymmetric Mannich reaction using a novel axially chiral amino sulfonamide (S)-3 that is highly anti- and enantioselective has been developed. For instance, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and alpha-imino esters proceeded smoothly to give anti Mannich products with a significantly higher anti/syn ratio and enantioselectivity than previously possible. By utilizing N-Boc-protected aromatic imines instead of alpha-imino esters, the synthetically useful Boc protecting group and various aromatic or heteroaromatic substituents were installed into the anti Mannich products and consequently the substrate scope of the anti-selective Mannich reaction and the synthetic utility of the anti Mannich products have been expanded. The axially chiral amino sulfonamide (S)-3 has also been successfully applied to asymmetric direct cross-aldol reaction between two different aldehydes. The catalyst (S)-3 has the advantage of giving mainly syn products, whereas proline shows the opposite anti selectivity.

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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

Maruoka K

No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19479934

Citation

Kano, Taichi, et al. "A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Anti-selective Mannich Reactions and Syn-selective Cross-aldol Reactions." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 15, no. 27, 2009, pp. 6678-87.

Kano T, Yamaguchi Y, Maruoka K. A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric anti-selective Mannich reactions and syn-selective cross-aldol reactions. Chemistry. 2009;15(27):6678-87.

Kano, T., Yamaguchi, Y., & Maruoka, K. (2009). A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric anti-selective Mannich reactions and syn-selective cross-aldol reactions. Chemistry (Weinheim an Der Bergstrasse, Germany), 15(27), 6678-87. https://doi.org/10.1002/chem.200900267

Kano T, Yamaguchi Y, Maruoka K. A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Anti-selective Mannich Reactions and Syn-selective Cross-aldol Reactions. Chemistry. 2009 Jul 6;15(27):6678-87. PubMed PMID: 19479934.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric anti-selective Mannich reactions and syn-selective cross-aldol reactions. AU - Kano,Taichi, AU - Yamaguchi,Yukako, AU - Maruoka,Keiji, PY - 2009/5/30/entrez PY - 2009/5/30/pubmed PY - 2009/5/30/medline SP - 6678 EP - 87 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 15 IS - 27 N2 - A direct asymmetric Mannich reaction using a novel axially chiral amino sulfonamide (S)-3 that is highly anti- and enantioselective has been developed. For instance, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and alpha-imino esters proceeded smoothly to give anti Mannich products with a significantly higher anti/syn ratio and enantioselectivity than previously possible. By utilizing N-Boc-protected aromatic imines instead of alpha-imino esters, the synthetically useful Boc protecting group and various aromatic or heteroaromatic substituents were installed into the anti Mannich products and consequently the substrate scope of the anti-selective Mannich reaction and the synthetic utility of the anti Mannich products have been expanded. The axially chiral amino sulfonamide (S)-3 has also been successfully applied to asymmetric direct cross-aldol reaction between two different aldehydes. The catalyst (S)-3 has the advantage of giving mainly syn products, whereas proline shows the opposite anti selectivity. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/19479934/A_designer_axially_chiral_amino_sulfonamide_as_an_efficient_organocatalyst_for_direct_asymmetric_anti_selective_Mannich_reactions_and_syn_selective_cross_aldol_reactions_ L2 - https://doi.org/10.1002/chem.200900267 DB - PRIME DP - Unbound Medicine ER -

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A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric anti-selective Mannich reactions and syn-selective cross-aldol reactions.Chemistry. 2009 Jul 06; 15(27):6678-87.C