An efficient diastereoselective route to differentially protected anti-4-amino-1-alken-3-ols.
Zinc-promoted hydroxyallylation of alpha-amidoalkyl arylsulfones 4 using 3-bromo-propenyl methyl carbonate 5 proceeds smoothly in DMF at room temperature to afford high yields of differentially protected anti-1,2-amino alcohols 6.
Lombardo
Marco
M
Dipartimento di Chimica G. Ciamician, Università di Bologna, via Selmi 2, I-40126 Bologna, Italy. marco.lombardo@unibo.it
Mosconi
Elisa
E
Pasi
Filippo
F
Petrini
Marino
M
Trombini
Claudio
C
D000475:Alkenes / Q000138:chemical synthesis*; D000605:Amino Alcohols / Q000138:chemical synthesis*; D002384:Catalysis; D008401:Gas Chromatography-Mass Spectrometry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000475:Alkenes; D000605:Amino Alcohols; D007202:Indicators and Reagents; D015032:Zinc