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Asymmetric syn-selective Henry reaction catalyzed by the sulfonyldiamine-CuCl-pyridine system.
J Org Chem. 2008 Jul 04; 73(13):4903-6.JO

Abstract

A catalytic asymmetric Henry reaction has been developed with use of a sulfonyldiamine-CuCl complex as a catalyst. A series of new binaphthyl-containing sulfonyldiamine ligands (2a-h) were readily synthesized in two steps starting from commercially available chiral 1,2-diamines. The (R,R)-diamine-(R)-binaphthyl ligand (2d)-CuCl complex smoothly catalyzed the enantioselective Henry reaction with the assistance of pyridine to give the corresponding adduct with high enantiomeric excess (up to 93%). Moreover, the 2d-CuCl-pyridine system promotes the diastereoselective Henry reaction in syn-selective manner to give the adduct in up to 99% yield with 92:8 syn/ anti selectivity. The enantiomeric excess of the syn-adduct was 84% ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Arai T
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan. tarai@faculty.chiba-u.jp
Takashita R
No affiliation info available
Endo Y
No affiliation info available
Watanabe M
No affiliation info available
Yanagisawa A
No affiliation info available

MeSH

CatalysisCopperMolecular ConformationMolecular StructurePyridines

Pub Type(s)

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

Language

eng

PubMed ID

18512989

Citation

Arai, Takayoshi, et al. "Asymmetric Syn-selective Henry Reaction Catalyzed By the sulfonyldiamine-CuCl-pyridine System." The Journal of Organic Chemistry, vol. 73, no. 13, 2008, pp. 4903-6.
Arai T, Takashita R, Endo Y, et al. Asymmetric syn-selective Henry reaction catalyzed by the sulfonyldiamine-CuCl-pyridine system. J Org Chem. 2008;73(13):4903-6.
Arai, T., Takashita, R., Endo, Y., Watanabe, M., & Yanagisawa, A. (2008). Asymmetric syn-selective Henry reaction catalyzed by the sulfonyldiamine-CuCl-pyridine system. The Journal of Organic Chemistry, 73(13), 4903-6. https://doi.org/10.1021/jo800412x
Arai T, et al. Asymmetric Syn-selective Henry Reaction Catalyzed By the sulfonyldiamine-CuCl-pyridine System. J Org Chem. 2008 Jul 4;73(13):4903-6. PubMed PMID: 18512989.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric syn-selective Henry reaction catalyzed by the sulfonyldiamine-CuCl-pyridine system. AU - Arai,Takayoshi, AU - Takashita,Ryuta, AU - Endo,Yoko, AU - Watanabe,Masahiko, AU - Yanagisawa,Akira, Y1 - 2008/05/31/ PY - 2008/6/3/pubmed PY - 2008/9/24/medline PY - 2008/6/3/entrez SP - 4903 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 13 N2 - A catalytic asymmetric Henry reaction has been developed with use of a sulfonyldiamine-CuCl complex as a catalyst. A series of new binaphthyl-containing sulfonyldiamine ligands (2a-h) were readily synthesized in two steps starting from commercially available chiral 1,2-diamines. The (R,R)-diamine-(R)-binaphthyl ligand (2d)-CuCl complex smoothly catalyzed the enantioselective Henry reaction with the assistance of pyridine to give the corresponding adduct with high enantiomeric excess (up to 93%). Moreover, the 2d-CuCl-pyridine system promotes the diastereoselective Henry reaction in syn-selective manner to give the adduct in up to 99% yield with 92:8 syn/ anti selectivity. The enantiomeric excess of the syn-adduct was 84% ee. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/18512989/Asymmetric_syn_selective_Henry_reaction_catalyzed_by_the_sulfonyldiamine_CuCl_pyridine_system_ L2 - https://doi.org/10.1021/jo800412x DB - PRIME DP - Unbound Medicine ER -