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Enantioselective aldol reaction between isatins and cyclohexanone catalyzed by amino acid sulphonamides.
Chirality. 2015 Apr; 27(4):314-9.C

Abstract

Sulphonamides derived from primary α-amino acid were successfully applied to catalyze the aldol reaction between isatin and cyclohexanone under neat conditions. More interestingly, molecular sieves, as privileged additives, were found to play a vital role in achieving high enantioselectivity. Consequently, high yields (up to 99%) along with good enantioselectivities (up to 92% ee) and diastereoselectivities (up to 95:5 dr) were obtained. In addition, this reaction was also conveniently scaled up, demonstrating the applicability of this protocol.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang J
College of Chemistry and Chemical Engineering, Central South University, Changsha, P.R. China.
Liu Q
No affiliation info available
Hao Q
No affiliation info available
Sun Y
No affiliation info available
Luo Y
No affiliation info available
Yang H
No affiliation info available

MeSH

Amino AcidsCatalysisCyclohexanonesIsatinStereoisomerismSulfonamides

Pub Type(s)

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

Language

eng

PubMed ID

25691447

Citation

Wang, Jun, et al. "Enantioselective Aldol Reaction Between Isatins and Cyclohexanone Catalyzed By Amino Acid Sulphonamides." Chirality, vol. 27, no. 4, 2015, pp. 314-9.
Wang J, Liu Q, Hao Q, et al. Enantioselective aldol reaction between isatins and cyclohexanone catalyzed by amino acid sulphonamides. Chirality. 2015;27(4):314-9.
Wang, J., Liu, Q., Hao, Q., Sun, Y., Luo, Y., & Yang, H. (2015). Enantioselective aldol reaction between isatins and cyclohexanone catalyzed by amino acid sulphonamides. Chirality, 27(4), 314-9. https://doi.org/10.1002/chir.22433
Wang J, et al. Enantioselective Aldol Reaction Between Isatins and Cyclohexanone Catalyzed By Amino Acid Sulphonamides. Chirality. 2015;27(4):314-9. PubMed PMID: 25691447.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective aldol reaction between isatins and cyclohexanone catalyzed by amino acid sulphonamides. AU - Wang,Jun, AU - Liu,Qi, AU - Hao,Qing, AU - Sun,Yanhua, AU - Luo,Yiming, AU - Yang,Hua, Y1 - 2015/02/17/ PY - 2014/11/04/received PY - 2014/12/23/revised PY - 2015/01/16/accepted PY - 2015/2/19/entrez PY - 2015/2/19/pubmed PY - 2015/12/15/medline KW - 3-cycloalkanone-3-hydroxy-2-oxindole KW - asymmetric synthesis KW - molecular sieves KW - neat conditions KW - organocatalysis SP - 314 EP - 9 JF - Chirality JO - Chirality VL - 27 IS - 4 N2 - Sulphonamides derived from primary α-amino acid were successfully applied to catalyze the aldol reaction between isatin and cyclohexanone under neat conditions. More interestingly, molecular sieves, as privileged additives, were found to play a vital role in achieving high enantioselectivity. Consequently, high yields (up to 99%) along with good enantioselectivities (up to 92% ee) and diastereoselectivities (up to 95:5 dr) were obtained. In addition, this reaction was also conveniently scaled up, demonstrating the applicability of this protocol. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/25691447/Enantioselective_aldol_reaction_between_isatins_and_cyclohexanone_catalyzed_by_amino_acid_sulphonamides_ DB - PRIME DP - Unbound Medicine ER -