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Sterically and electronically tunable and bifunctional organocatalysts: design and application in asymmetric aldol reaction of cyclic ketones with aldehydes.
J Org Chem. 2006 Oct 13; 71(21):8198-202.JO

Abstract

Sterically and electronically tunable and bifunctional organocatalysts have been developed and evaluated in the direct aldol reaction of heterocyclic ketones. Catalysts with different substituents showed variable catalytic efficiency for analogous substrates, indicating the importance of fine-tuning the strength of the hydrogen bonding in the two NH groups. The reactions all proceeded in good to high yield and with excellent enantioselectivities ranging from 90% to >99% ee. In most cases, high diastereoselectivities ranging from 96/4 to 99/1 were obtained for the anti aldol adduct.

Authors+Show Affiliations

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

17025312

Citation

Chen, Jia-Rong, et al. "Sterically and Electronically Tunable and Bifunctional Organocatalysts: Design and Application in Asymmetric Aldol Reaction of Cyclic Ketones With Aldehydes." The Journal of Organic Chemistry, vol. 71, no. 21, 2006, pp. 8198-202.
Chen JR, Li XY, Xing XN, et al. Sterically and electronically tunable and bifunctional organocatalysts: design and application in asymmetric aldol reaction of cyclic ketones with aldehydes. J Org Chem. 2006;71(21):8198-202.
Chen, J. R., Li, X. Y., Xing, X. N., & Xiao, W. J. (2006). Sterically and electronically tunable and bifunctional organocatalysts: design and application in asymmetric aldol reaction of cyclic ketones with aldehydes. The Journal of Organic Chemistry, 71(21), 8198-202.
Chen JR, et al. Sterically and Electronically Tunable and Bifunctional Organocatalysts: Design and Application in Asymmetric Aldol Reaction of Cyclic Ketones With Aldehydes. J Org Chem. 2006 Oct 13;71(21):8198-202. PubMed PMID: 17025312.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sterically and electronically tunable and bifunctional organocatalysts: design and application in asymmetric aldol reaction of cyclic ketones with aldehydes. AU - Chen,Jia-Rong, AU - Li,Xin-Yong, AU - Xing,Xiao-Ning, AU - Xiao,Wen-Jing, PY - 2006/10/10/pubmed PY - 2007/8/8/medline PY - 2006/10/10/entrez SP - 8198 EP - 202 JF - The Journal of organic chemistry JO - J Org Chem VL - 71 IS - 21 N2 - Sterically and electronically tunable and bifunctional organocatalysts have been developed and evaluated in the direct aldol reaction of heterocyclic ketones. Catalysts with different substituents showed variable catalytic efficiency for analogous substrates, indicating the importance of fine-tuning the strength of the hydrogen bonding in the two NH groups. The reactions all proceeded in good to high yield and with excellent enantioselectivities ranging from 90% to >99% ee. In most cases, high diastereoselectivities ranging from 96/4 to 99/1 were obtained for the anti aldol adduct. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17025312/Sterically_and_electronically_tunable_and_bifunctional_organocatalysts:_design_and_application_in_asymmetric_aldol_reaction_of_cyclic_ketones_with_aldehydes_ L2 - https://doi.org/10.1021/jo0615089 DB - PRIME DP - Unbound Medicine ER -
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