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Asymmetric direct aldol reactions of acetoacetals catalyzed by a simple chiral primary amine.
J Org Chem. 2009 Dec 18; 74(24):9521-3.JO

Abstract

An asymmetric direct aldol reaction of acetoacetals is described. Under the catalysis of a simple chiral primary amine, the direct aldol reactions of acetoacetals occur exclusively on the gamma-position to give vinylogous-type aldol products with high diastereo- and enantioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Luo S
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China. luosz@iccas.ac.cn
Qiao Y
No affiliation info available
Zhang L
No affiliation info available
Li J
No affiliation info available
Li X
No affiliation info available
Cheng JP
No affiliation info available

MeSH

AcetalsAcetatesAldehydesAminesBiological ProductsCatalysisChromatography, High Pressure LiquidKetonesMacrolidesMagnetic Resonance SpectroscopySolventsStereoisomerismVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

19883088

Citation

Luo, Sanzhong, et al. "Asymmetric Direct Aldol Reactions of Acetoacetals Catalyzed By a Simple Chiral Primary Amine." The Journal of Organic Chemistry, vol. 74, no. 24, 2009, pp. 9521-3.
Luo S, Qiao Y, Zhang L, et al. Asymmetric direct aldol reactions of acetoacetals catalyzed by a simple chiral primary amine. J Org Chem. 2009;74(24):9521-3.
Luo, S., Qiao, Y., Zhang, L., Li, J., Li, X., & Cheng, J. P. (2009). Asymmetric direct aldol reactions of acetoacetals catalyzed by a simple chiral primary amine. The Journal of Organic Chemistry, 74(24), 9521-3. https://doi.org/10.1021/jo9021259
Luo S, et al. Asymmetric Direct Aldol Reactions of Acetoacetals Catalyzed By a Simple Chiral Primary Amine. J Org Chem. 2009 Dec 18;74(24):9521-3. PubMed PMID: 19883088.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric direct aldol reactions of acetoacetals catalyzed by a simple chiral primary amine. AU - Luo,Sanzhong, AU - Qiao,Yupu, AU - Zhang,Long, AU - Li,Jiuyuan, AU - Li,Xin, AU - Cheng,Jin-Pei, PY - 2009/11/4/entrez PY - 2009/11/4/pubmed PY - 2010/3/20/medline SP - 9521 EP - 3 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 24 N2 - An asymmetric direct aldol reaction of acetoacetals is described. Under the catalysis of a simple chiral primary amine, the direct aldol reactions of acetoacetals occur exclusively on the gamma-position to give vinylogous-type aldol products with high diastereo- and enantioselectivity. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19883088/Asymmetric_direct_aldol_reactions_of_acetoacetals_catalyzed_by_a_simple_chiral_primary_amine_ L2 - https://doi.org/10.1021/jo9021259 DB - PRIME DP - Unbound Medicine ER -