ENANTIOMERICALLY PURE BETA-AMINO SULFIDES AND BETA-AMINO THIOLS FROM EPHEDRINE

Authors
POELERT MA HOF RP PEPER NCMW KELLOGG RM
Citation
Ma. Poelert et al., ENANTIOMERICALLY PURE BETA-AMINO SULFIDES AND BETA-AMINO THIOLS FROM EPHEDRINE, Heterocycles, 37(1), 1994, pp. 461-475
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
37
Issue
1
Year of publication
1994
Pages
461 - 475
Database
ISI
SICI code
0385-5414(1994)37:1<461:EPBSAB>2.0.ZU;2-O
Abstract
Ephedrine and pseudoephedrine are converted by means of a Mitsunobu re action to respectively trans- and cis-aziridines, which can be ring-op ened at the benzylic center with inversion of configuration by thiols and thiol acids. The trans-aziridine from ephedrine reacts also with H 2S in acetone under which conditions the amino thiol is trapped as the thiazolane. The same aziridine also undergoes cycloaddition with CS2.