(2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine
نویسندگان
چکیده
The reaction of a sulfur ylide with a chiral non-racemic sulfinyl imine afforded the desired aziridine in excellent yield and subsequent oxidation of the sulfinyl moiety dissolved in anhydrous dichloro-methane using a 75% aqueous solution of 3-chloro-per-oxy-benzoic acid afforded the title compound, C(14)H(27)NO(6)S. The configuration of the newly formed stereogenic center at the point of attachment of the 1,4-dioxane ring to the aziridine ring is S. The configurations of the pre-existing sites 2-, 5-, and 6-positions of the 1,4-dioxane ring prior to reaction of sulfinyl imine with the sulfur ylide are S, R, and R, respectively. The C-N bond lengths of the aziridine are 1.478 (2) and 1.486 (2) Å.
منابع مشابه
Comparison of various density functional methods for distinguishing stereoisomers based on computed (1)H or (13)C NMR chemical shifts using diastereomeric penam beta-lactams as a test set.
Full (1)H and (13)C NMR chemical shift assignments were made for two sets of penam beta-lactams: namely, the diastereomeric (2S, 5S, 6S)-, (2S, 5R, 6R)-, (2S, 5S, 6R)-, and (2S, 5R, 6S)-methyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylates (1-4) and (2S, 5R, 6R)-, (2S, 5S, 6R)-, and (2S, 5R, 6S)-6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4...
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