Allylation of aldehydes and imines: promoted by reuseable polymer-supported sulfonamide of N-glycine.
[reaction: see text] A allylation of aldehydes and imines (generated in situ from aldehydes and amines) with allyltributyltin promoted by recoverable and reusable the polymer-supported sulfonamide of N-glycine has been developed. Good to high yields were obtained in various cases. Most of the SnBu(3) residue can be recovered as Bu(3)SnCl. Highly stereoselective synthesis of N-Boc-(2S,3S)-3-hydroxy-2-phenylpiperidine 7 was achieved by using the P4a-mediated allylation of Boc-l-phenylglycinal as a key step.
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 FengLin Lu, Shanghai 200032, China.
Gui-long
GL
Li
Gang
G
Zhao
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis*; D011108:Polymers / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
D000447:Aldehydes; D007097:Imines; C514303:N-Boc-(2S,3S)-3-hydroxy-2-phenylpiperidine; D009947:Organotin Compounds; D010880:Piperidines; D011108:Polymers; D013449:Sulfonamides; D005998:Glycine