207276-92-4Relevant academic research and scientific papers
Reversal of diastereofacial selectivity in the nucleophilic addition reaction to chiral N-sulfinimine and application to the synthesis of indrizidine 223AB
Koriyama, Yuji,Nozawa, Akihiro,Hayakawa, Ryuuichirou,Shimizu, Makoto
, p. 9621 - 9628 (2007/10/03)
Diastereoselective addition reaction of ester enolates and Grignard reagents to optically active N-sulfinimines was examined. Reversal of the diastereofacial selectivity was realized by using appropriate metal species, solvents and additives, and the β-amino esters (up to >98% de) and the homoallylic amines (up to >98% de) were obtained in good yields. β-Amino esters thus obtained were converted to the useful β-amino acids involving (R)-homoserine. Application to the synthesis of indrizidine alkaloids was also described.
