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A highly efficient organocatalyst for direct aldol reactions of ketones with aldehydes [corrected].
J Am Chem Soc. 2005 Jun 29; 127(25):9285-9.JA

Abstract

L-proline amides derived from various chiral beta-amino alcohols that bear substituents with various electron natures at their stereogenic centers are prepared and evaluated for catalyzing the direct Aldol reaction of 4-nitrobenzaldehyde with acetone. Catalysts with strong electron-withdrawing groups are found to exhibit higher catalytic activity and enantioselectivity than their analogues with electron-donating groups. The presence of 2 mol % catalyst 4g significantly catalyzes the direct Aldol reactions of a wide range of aldehydes with acetone and butanone, to give the beta-hydroxy ketones with very high enantioselectivities ranging from 96% to >99% ee. High diastereoselectivity of 95/5 was observed for the anti Aldol product from the reaction of cyclohexanone, and excellent enantioselectivity of 93% ee was provided for anti Aldol product from the reaction of cyclopentanone.

Authors+Show Affiliations

Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo 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

15969611

Citation

Tang, Zhuo, et al. "A Highly Efficient Organocatalyst for Direct Aldol Reactions of Ketones With Aldehydes [corrected]." Journal of the American Chemical Society, vol. 127, no. 25, 2005, pp. 9285-9.
Tang Z, Yang ZH, Chen XH, et al. A highly efficient organocatalyst for direct aldol reactions of ketones with aldehydes [corrected]. J Am Chem Soc. 2005;127(25):9285-9.
Tang, Z., Yang, Z. H., Chen, X. H., Cun, L. F., Mi, A. Q., Jiang, Y. Z., & Gong, L. Z. (2005). A highly efficient organocatalyst for direct aldol reactions of ketones with aldehydes [corrected]. Journal of the American Chemical Society, 127(25), 9285-9.
Tang Z, et al. A Highly Efficient Organocatalyst for Direct Aldol Reactions of Ketones With Aldehydes [corrected]. J Am Chem Soc. 2005 Jun 29;127(25):9285-9. PubMed PMID: 15969611.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A highly efficient organocatalyst for direct aldol reactions of ketones with aldehydes [corrected]. AU - Tang,Zhuo, AU - Yang,Zhi-Hua, AU - Chen,Xiao-Hua, AU - Cun,Lin-Feng, AU - Mi,Ai-Qiao, AU - Jiang,Yao-Zhong, AU - Gong,Liu-Zhu, PY - 2005/6/23/pubmed PY - 2005/10/27/medline PY - 2005/6/23/entrez SP - 9285 EP - 9 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 127 IS - 25 N2 - L-proline amides derived from various chiral beta-amino alcohols that bear substituents with various electron natures at their stereogenic centers are prepared and evaluated for catalyzing the direct Aldol reaction of 4-nitrobenzaldehyde with acetone. Catalysts with strong electron-withdrawing groups are found to exhibit higher catalytic activity and enantioselectivity than their analogues with electron-donating groups. The presence of 2 mol % catalyst 4g significantly catalyzes the direct Aldol reactions of a wide range of aldehydes with acetone and butanone, to give the beta-hydroxy ketones with very high enantioselectivities ranging from 96% to >99% ee. High diastereoselectivity of 95/5 was observed for the anti Aldol product from the reaction of cyclohexanone, and excellent enantioselectivity of 93% ee was provided for anti Aldol product from the reaction of cyclopentanone. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/15969611/A_highly_efficient_organocatalyst_for_direct_aldol_reactions_of_ketones_with_aldehydes_[corrected]_ L2 - https://dx.doi.org/10.1021/ja0510156 DB - PRIME DP - Unbound Medicine ER -