Optically active N-sulfinimines underwent stereoselective Michael/nucleophilic addition domino reaction triggered by magnesium thiolate to give alpha-phenylthiomethyl-beta-(N-sulfinylamino) esters in high diastereomeric excess. The adducts were readily converted into optically active alpha-methylene-beta-(N-sulfinylamino)esters so that this reaction provides a useful asymmetric aza-Baylis-Hillman-equivalent method.

Aminocarboxylic acids (hydrazinocarboxylic acids) and esters Q 0440Asymmetric Thio-Michael/Nucleophilic Addition Domino Reaction with Chiral N-Sulfinimines. -The reaction offers a general and effective access to α-functionalized β-amino esters. Subsequent dethiolation leads to various chiral β-amino-α-methylene esters. The domino products can also be converted into β-lactams like (VIII).-(KAMIMURA*, A.; OKAWA, H.; MORISAKI, Y.; ISHIKAWA, S.; UNO, H.; J. Org. Chem. 72 (2007) 9, 3569-3572; Dep. Appl. Mol. Biosci., Grad. Sch. Med., Yamaguchi Univ., Ube, Yamaguchi 755, Japan; Eng.) -Jannicke 34-079