New asymmetric halo aldol reaction provides a novel approach to biologically important chiral cyclothers and cycloamines.
[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.
Timmons
Cody
C
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
Chen
Dianjun
D
Cannon
John F
JF
Headley
Allan D
AD
Li
Guigen
G
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008956:Models, Chemical; D008968:Molecular Conformation; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines; D005663:Furans; D007659:Ketones; C018674:tetrahydrofuran