Tags

Type your tag names separated by a space and hit enter

A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric mannich reactions of N-Boc-protected imines.
Angew Chem Int Ed Engl. 2009; 48(10):1838-40.AC

Abstract

The moderate nucleophilicity of the axially chiral amino sulfonamide (S)-1 suppresses the problematic side reactions, including aldol reactions, in the asymmetric Mannich reaction of N-Boc-protected imines with aldehydes. The corresponding adducts are obtained in good yield and excellent stereoselectivity (see scheme; Boc = tert-butoxycarbonyl, Tf = trifluoromethanesulfonyl).

Links

Publisher Full Text (DOI)

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

MeSH

AldehydesCatalysisIminesMannich BasesNitrogenStereoisomerismSulfonamides

Pub Type(s)

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

Language

eng

PubMed ID

19173354

Citation

Kano, Taichi, et al. "A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N-Boc-protected Imines." Angewandte Chemie (International Ed. in English), vol. 48, no. 10, 2009, pp. 1838-40.
Kano T, Yamaguchi Y, Maruoka K. A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric mannich reactions of N-Boc-protected imines. Angew Chem Int Ed Engl. 2009;48(10):1838-40.
Kano, T., Yamaguchi, Y., & Maruoka, K. (2009). A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric mannich reactions of N-Boc-protected imines. Angewandte Chemie (International Ed. in English), 48(10), 1838-40. https://doi.org/10.1002/anie.200805628
Kano T, Yamaguchi Y, Maruoka K. A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N-Boc-protected Imines. Angew Chem Int Ed Engl. 2009;48(10):1838-40. PubMed PMID: 19173354.
* 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 mannich reactions of N-Boc-protected imines. AU - Kano,Taichi, AU - Yamaguchi,Yukako, AU - Maruoka,Keiji, PY - 2009/1/29/entrez PY - 2009/1/29/pubmed PY - 2009/4/3/medline SP - 1838 EP - 40 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 48 IS - 10 N2 - The moderate nucleophilicity of the axially chiral amino sulfonamide (S)-1 suppresses the problematic side reactions, including aldol reactions, in the asymmetric Mannich reaction of N-Boc-protected imines with aldehydes. The corresponding adducts are obtained in good yield and excellent stereoselectivity (see scheme; Boc = tert-butoxycarbonyl, Tf = trifluoromethanesulfonyl). SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/19173354/A_designer_axially_chiral_amino_sulfonamide_as_an_efficient_organocatalyst_for_direct_asymmetric_mannich_reactions_of_N_Boc_protected_imines_ L2 - https://doi.org/10.1002/anie.200805628 DB - PRIME DP - Unbound Medicine ER -