175849-95-3

Upstream product

• 175849-90-8 (S)-N-<4-Bromo-1-(4-methoxyphenyl)butan-2-yl>oxazolidine-2,4-dione 
• 175849-87-3 (R)-4-Bromo-1-(4-methoxyphenyl)butan-2-ol 
• 13139-86-1 4-methoxyphenyl magnesium bromide 

Relevant academic research and scientific papers

Highly diastereoselective route to trans-S-substituted 2-hydroxymethylpyrrolidine derivatives by radical cyclisation

The cyclisation of radical species generated from (S)-N-(3-bromopropyl)oxazolin-2-ones 22 by treatment with tributylstannane in the presence of AIBN yielded 5-substituted pyrrolooxazolones with high diastereoselectivity. In the same reaction using (±)-N-(3-bromobutyl)oxazolin-2-one 25a or (±)-N-(4-bromopentan-2-yl)oxazolin-2-one 25b, the radical cyclisation gave predominantly the (5S*,7S*,7aR*)-5,7-disubstituted pyrrolooxazolines rather than the (5S*,7R*,7aR*) products. The radical cyclisation of 4-phenylsulfanyloxazolidinones 29a,b also resulted in the predominant formation of the corresponding (5S,7S,7aR)-5,7-disubstituted pyrrolooxazolidine derivatives.