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New asymmetric halo aldol reaction provides a novel approach to biologically important chiral cyclothers and cycloamines.
Org Lett. 2004 Jun 10; 6(12):2075-8.OL

Abstract

[reaction: see text] A new asymmetric halo aldol reaction has been developed by reacting cyclopropyl carbonyl derived enolates with aldehydes. The absolute structure was unambiguously confirmed by X-ray structural analysis. Eight examples were reported with good yields and up to complete control of diastereomeric excesses. These halo aldol products have been readily cyclized in the presence of weak bases to produce chiral 2,3-disubstituted tetrahydrofuran derivatives in good yield without any observed epimerization.

Authors+Show Affiliations

Timmons C
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
Chen D
No affiliation info available
Cannon JF
No affiliation info available
Headley AD
No affiliation info available
Li G
No affiliation info available

MeSH

AldehydesAminesCyclizationFuransKetonesModels, ChemicalMolecular ConformationStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15176822

Citation

Timmons, Cody, et al. "New Asymmetric Halo Aldol Reaction Provides a Novel Approach to Biologically Important Chiral Cyclothers and Cycloamines." Organic Letters, vol. 6, no. 12, 2004, pp. 2075-8.
Timmons C, Chen D, Cannon JF, et al. New asymmetric halo aldol reaction provides a novel approach to biologically important chiral cyclothers and cycloamines. Org Lett. 2004;6(12):2075-8.
Timmons, C., Chen, D., Cannon, J. F., Headley, A. D., & Li, G. (2004). New asymmetric halo aldol reaction provides a novel approach to biologically important chiral cyclothers and cycloamines. Organic Letters, 6(12), 2075-8.
Timmons C, et al. New Asymmetric Halo Aldol Reaction Provides a Novel Approach to Biologically Important Chiral Cyclothers and Cycloamines. Org Lett. 2004 Jun 10;6(12):2075-8. PubMed PMID: 15176822.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - New asymmetric halo aldol reaction provides a novel approach to biologically important chiral cyclothers and cycloamines. AU - Timmons,Cody, AU - Chen,Dianjun, AU - Cannon,John F, AU - Headley,Allan D, AU - Li,Guigen, PY - 2004/6/5/pubmed PY - 2005/4/2/medline PY - 2004/6/5/entrez SP - 2075 EP - 8 JF - Organic letters JO - Org Lett VL - 6 IS - 12 N2 - [reaction: see text] A new asymmetric halo aldol reaction has been developed by reacting cyclopropyl carbonyl derived enolates with aldehydes. The absolute structure was unambiguously confirmed by X-ray structural analysis. Eight examples were reported with good yields and up to complete control of diastereomeric excesses. These halo aldol products have been readily cyclized in the presence of weak bases to produce chiral 2,3-disubstituted tetrahydrofuran derivatives in good yield without any observed epimerization. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15176822/New_asymmetric_halo_aldol_reaction_provides_a_novel_approach_to_biologically_important_chiral_cyclothers_and_cycloamines_ DB - PRIME DP - Unbound Medicine ER -