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Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: unprecedented regiocontrol in aqueous media.
Org Lett. 2004 Jun 24; 6(13):2285-7.OL

Abstract

[reaction: see text] L-Proline-based small peptides have been developed as efficient catalysts for the asymmetric direct aldol reactions of hydroxyacetone with aldehydes. Chiral 1,4-diols 7, which are disfavored products in similar aldol reactions catalyzed by either aldolases or L-proline, were obtained in high yields and enantioselectivities of up to 96% ee with peptides 3 and 4 in aqueous media.

Authors+Show Affiliations

Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, 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 available

Pub Type(s)

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

Language

eng

PubMed ID

15200341

Citation

Tang, Zhuo, et al. "Small Peptides Catalyze Highly Enantioselective Direct Aldol Reactions of Aldehydes With Hydroxyacetone: Unprecedented Regiocontrol in Aqueous Media." Organic Letters, vol. 6, no. 13, 2004, pp. 2285-7.
Tang Z, Yang ZH, Cun LF, et al. Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: unprecedented regiocontrol in aqueous media. Org Lett. 2004;6(13):2285-7.
Tang, Z., Yang, Z. H., Cun, L. F., Gong, L. Z., Mi, A. Q., & Jiang, Y. Z. (2004). Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: unprecedented regiocontrol in aqueous media. Organic Letters, 6(13), 2285-7.
Tang Z, et al. Small Peptides Catalyze Highly Enantioselective Direct Aldol Reactions of Aldehydes With Hydroxyacetone: Unprecedented Regiocontrol in Aqueous Media. Org Lett. 2004 Jun 24;6(13):2285-7. PubMed PMID: 15200341.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: unprecedented regiocontrol in aqueous media. AU - Tang,Zhuo, AU - Yang,Zhi-Hua, AU - Cun,Lin-Feng, AU - Gong,Liu-Zhu, AU - Mi,Ai-Qiao, AU - Jiang,Yao-Zhong, PY - 2004/6/18/pubmed PY - 2005/5/10/medline PY - 2004/6/18/entrez SP - 2285 EP - 7 JF - Organic letters JO - Org Lett VL - 6 IS - 13 N2 - [reaction: see text] L-Proline-based small peptides have been developed as efficient catalysts for the asymmetric direct aldol reactions of hydroxyacetone with aldehydes. Chiral 1,4-diols 7, which are disfavored products in similar aldol reactions catalyzed by either aldolases or L-proline, were obtained in high yields and enantioselectivities of up to 96% ee with peptides 3 and 4 in aqueous media. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15200341/Small_peptides_catalyze_highly_enantioselective_direct_aldol_reactions_of_aldehydes_with_hydroxyacetone:_unprecedented_regiocontrol_in_aqueous_media_ L2 - https://doi.org/10.1021/ol049141m DB - PRIME DP - Unbound Medicine ER -