(2S,3R,4S,5R)-Diethyl 2-(10,10-dimethyl-3,3-dioxo-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decan-4-ylcarbonyl)-5-phenylpyrrolidine-3,4-dicarboxylate: a novel isomorphous-by-addition compound.
The title compound, C(27)H(36)N(2)O(7)S, (I), is isomorphous by addition with the dimethyl ester analogue [Garner, Dogan, Youngs, Kennedy, Protasiewicz & Zaniewski (2001). Tetrahedron, 57, 71-85], (II), by replacing two methyl ester H atoms with two methyl groups. With the exception of the conformation of one of the ester groups, the molecules are almost superimposable. Likewise, apart from a slightly larger c axis in (I), few differences in the cell packing of (I) and (II) are found, with both dominated by the same C-H...O hydrogen bonds. Full synthetic and spectroscopic details of (I) are given. The molecular synthesis is important as an example of chiral auxiliary-assisted 1,3-dipolar cycloaddition of an azomethine ylid.
Gainsford
Graeme J
GJ
Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand.
Mee
Simon P H
SP
Luxenburger
Andreas
A
D003998:Dicarboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
C534340:(2S,3R,4S,5R)-diethyl 2-(10,10-dimethyl-3,3-dioxo-3lambda(6)-thia-4-azatricyclo(5.2.1.0(1,5))decan-4-ylcarbonyl)-5-phenylpyrrolidine-3,4-dicarboxylate; D003998:Dicarboxylic Acids; D006575:Heterocyclic Compounds, 3-Ring; D011759:Pyrrolidines