Reaction of optically active alpha-aminoallenylstannanes with aldehydes formed in situ from the Lewis-acid-catalyzed rearrangement of epoxides.
Reaction of optically active alpha-oxazolidinonylallenylstannanes with oxiranes in the presence of BF3.OEt2 produced beta-hydroxypropargylamines with high syn diastereoselectivity and high enantioselectivity through an initial Lewis-acid-catalyzed rearrangement of the oxirane to the corresponding aldehyde via an alkyl, aryl, or hydride shift. This permits the use of readily available oxiranes as alternatives to aldehydes that are difficult to prepare and/or unstable.
de Los Ríos
Cristóbal
C
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Hegedus
Louis S
LS
D000143:Acids / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D005027:Ethylene Oxide / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009904:Optical Rotation; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry*
D000143:Acids; D000447:Aldehydes; D004852:Epoxy Compounds; D017971:Tin Compounds; C031525:stannane; D005027:Ethylene Oxide