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Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones.
J Org Chem. 2008 Aug 01; 73(15):6006-9.JO

Abstract

A new class of organocatalysts has been designed by rational combination of proline with cinchona alkaloids. The chiral amine 3a, prepared from l-proline and cinchonidine, has been found to be an efficient catalyst for the direct aldol reactions of acetone or 2-butanone with a wide range of aldehydes (up to 98% ee). The cinchonidine backbone is essential to the reaction efficiency and enantioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chen JR
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
An XL
No affiliation info available
Zhu XY
No affiliation info available
Wang XF
No affiliation info available
Xiao WJ
No affiliation info available

MeSH

AldehydesAminesCatalysisKetonesMolecular StructureNitrobenzenesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

18572922

Citation

Chen, Jia-Rong, et al. "Rational Combination of Two Privileged Chiral Backbones: Highly Efficient Organocatalysts for Asymmetric Direct Aldol Reactions Between Aromatic Aldehydes and Acylic Ketones." The Journal of Organic Chemistry, vol. 73, no. 15, 2008, pp. 6006-9.
Chen JR, An XL, Zhu XY, et al. Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones. J Org Chem. 2008;73(15):6006-9.
Chen, J. R., An, X. L., Zhu, X. Y., Wang, X. F., & Xiao, W. J. (2008). Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones. The Journal of Organic Chemistry, 73(15), 6006-9. https://doi.org/10.1021/jo800910s
Chen JR, et al. Rational Combination of Two Privileged Chiral Backbones: Highly Efficient Organocatalysts for Asymmetric Direct Aldol Reactions Between Aromatic Aldehydes and Acylic Ketones. J Org Chem. 2008 Aug 1;73(15):6006-9. PubMed PMID: 18572922.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones. AU - Chen,Jia-Rong, AU - An,Xiao-Lei, AU - Zhu,Xiao-Yu, AU - Wang,Xu-Fan, AU - Xiao,Wen-Jing, Y1 - 2008/06/24/ PY - 2008/6/25/pubmed PY - 2008/9/27/medline PY - 2008/6/25/entrez SP - 6006 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 15 N2 - A new class of organocatalysts has been designed by rational combination of proline with cinchona alkaloids. The chiral amine 3a, prepared from l-proline and cinchonidine, has been found to be an efficient catalyst for the direct aldol reactions of acetone or 2-butanone with a wide range of aldehydes (up to 98% ee). The cinchonidine backbone is essential to the reaction efficiency and enantioselectivity. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/18572922/Rational_combination_of_two_privileged_chiral_backbones:_highly_efficient_organocatalysts_for_asymmetric_direct_aldol_reactions_between_aromatic_aldehydes_and_acylic_ketones_ L2 - https://doi.org/10.1021/jo800910s DB - PRIME DP - Unbound Medicine ER -