Tetrahedron

Reversal of diastereofacial selectivity in the nucleophilic addition reaction to chiral N-sulfinimine and application to the synthesis of indrizidine 223AB

Y Koriyama, A Nozawa, R Hayakawa, M Shimizu

Index: Koriyama, Yuji; Nozawa, Akihiro; Hayakawa, Ryuuichirou; Shimizu, Makoto Tetrahedron, 2002 , vol. 58, # 47 p. 9621 - 9628

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Citation Number: 46

Abstract

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 ...