N-[alpha-(2-Bromo-1-butenyl)-alpha-methyl]oxazolin-2-one (7) and N-[alpha-(2-bromo-1-butenyl)-alpha-pyranyloxyethyl]oxazolin-2-one (14), obtained by starting with ethyl acetoacetate, were treated with tributyltin hydride in the presence of AIBN afforded the cyclization products (8) and (15), respectively, with high diastereoselectivity. Conversion of the 8-methyleneoxazolidinopiperidine (15) to the 6-hydroxyethyl-2-hydroxymethyl-3-hydroxypiperidine derivative (18) was described.
机构:
Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, IndiaIndian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
Das, Biswanath
Damodar, Kongara
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Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, IndiaIndian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
Damodar, Kongara
Bhunia, Nisith
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Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, IndiaIndian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India