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Asymmetric synthesis of bicyclic piperidines via L-proline catalyzed aldol reaction of 3-phthalimidopropanal.
Chirality. 2008 Jun; 20(6):805-11.C

Abstract

A highly enantioselective approach for preparing optically active bicyclic piperidines is described. The key step for introducing chiral centers was a L-proline catalyzed direct enantioselective aldol reaction of 3-phthalimidopropanal with aliphatic ketones. In the reactions with alicyclic ketones, a highly enantioselective formation of anti-2-(3-phthalimido-1-hydroxypropyl)cycloketones 1a-1b (>99% ee) was observed. The aldol products 1 could be subsequently converted into bicyclic piperidines 2 via a consecutive reductive deprotection, acylation, ring closure, and hydrolysis.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhang F
Department of Chemistry, Huazhong University of Science and Technology, Hubei, China.
Peng Y
No affiliation info available
Gong Y
No affiliation info available

MeSH

AldehydesBridged Bicyclo CompoundsCatalysisChemistry, OrganicMagnetic Resonance SpectroscopyMolecular StructurePhthalimidesPiperidinesProlineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

18306293

Citation

Zhang, Fanglin, et al. "Asymmetric Synthesis of Bicyclic Piperidines Via L-proline Catalyzed Aldol Reaction of 3-phthalimidopropanal." Chirality, vol. 20, no. 6, 2008, pp. 805-11.
Zhang F, Peng Y, Gong Y. Asymmetric synthesis of bicyclic piperidines via L-proline catalyzed aldol reaction of 3-phthalimidopropanal. Chirality. 2008;20(6):805-11.
Zhang, F., Peng, Y., & Gong, Y. (2008). Asymmetric synthesis of bicyclic piperidines via L-proline catalyzed aldol reaction of 3-phthalimidopropanal. Chirality, 20(6), 805-11. https://doi.org/10.1002/chir.20549
Zhang F, Peng Y, Gong Y. Asymmetric Synthesis of Bicyclic Piperidines Via L-proline Catalyzed Aldol Reaction of 3-phthalimidopropanal. Chirality. 2008;20(6):805-11. PubMed PMID: 18306293.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis of bicyclic piperidines via L-proline catalyzed aldol reaction of 3-phthalimidopropanal. AU - Zhang,Fanglin, AU - Peng,Yiyuan, AU - Gong,Yuefa, PY - 2008/2/29/pubmed PY - 2008/6/28/medline PY - 2008/2/29/entrez SP - 805 EP - 11 JF - Chirality JO - Chirality VL - 20 IS - 6 N2 - A highly enantioselective approach for preparing optically active bicyclic piperidines is described. The key step for introducing chiral centers was a L-proline catalyzed direct enantioselective aldol reaction of 3-phthalimidopropanal with aliphatic ketones. In the reactions with alicyclic ketones, a highly enantioselective formation of anti-2-(3-phthalimido-1-hydroxypropyl)cycloketones 1a-1b (>99% ee) was observed. The aldol products 1 could be subsequently converted into bicyclic piperidines 2 via a consecutive reductive deprotection, acylation, ring closure, and hydrolysis. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/18306293/Asymmetric_synthesis_of_bicyclic_piperidines_via_L_proline_catalyzed_aldol_reaction_of_3_phthalimidopropanal_ DB - PRIME DP - Unbound Medicine ER -