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2005
Mercaptans
P 0430
31- 075
Asymmetric Induction in the Conjugate Addition of Thioacetic Acid to Methacrylamides with Chiral Auxiliaries. — Methacrylamide bearing a C2-symmetric
trans-2,5-disubstituted pyrrolidine as chiral auxiliary undergoes a highly diastereoselective addition reaction with thioacetic acid. Effective conditions are found to hydrolyze addition product (III) almost without racemization. The resulting mercapto acid
is a key intermediate for the antihypertensive compound captopril. The chiral auxiliary
can be recovered as the demethylated and N-Boc-protected form in good yield. Adduct
(VI) is quite resistant to several hydrolytic conditions. — (KIM, B. H.; LEE, H. B.;
HWANG, J. K.; KIM*, Y. G.; Tetrahedron: Asymmetry 16 (2005) 6, 1215-1220; Sch.
Chem. Eng., Seoul Natl. Univ., Seoul 151-744, S. Korea; Eng.) — Klein
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