ABSTRACT
The first diastereoselective synthesis of (-)-1-epi-lentiginosine from a common chiral trans-epoxyamide derived from 2-pyridincarbaldehyde is reported. This methodology involves a sequential oxirane ring opening and intramolecular 5-exo-tet cyclization of tosylate trans-epoxyalcohol to afford a diastereomeric mixture of indolizinium salts in a one-pot fashion, followed by regio- and diastereospecific pyridinium ring reduction.
ABSTRACT
The synthesis of new chiral highly functionalized zwitterionic bicyclic lactams starting from acyclic ß-enaminoesters derived from (R)-(-)-2-phenylglycinol is described. The key step involved an intramolecular non-classical Corey-Chaykovsky ring-closing reaction of the corresponding sulfonium salts derived from ß-enaminoesters. This methodology permits the generation of two or three new stereogenic centers with high diastereoselectivity. The utility of these intermediates was demonstrated by the stereocontrolled total synthesis of cis-4-hydroxy-2-methyl piperidine and its corresponding pipecolic acid derivative.
ABSTRACT
In the title compound C(17)H(25)NO(2), the piperidin-2-one ring adopts an envelope conformation with the C atom in the 5-position as the flap. The crystal packing is stabilized by inter-molecular O-Hâ¯O hydrogen bonds, building a infinite chain along the b-axis direction. C-Hâ¯π inter-actions further stabilize the crystal packing.
ABSTRACT
In the title compound, C(18)H(18)N(2)O, the dihedral angle between the indole system and the phenyl ring is 17.2â (2)°. The crystal packing features two N-Hâ¯O hydrogen bonds, which link the mol-ecules into layers parallel to (001). The absolute configuration was determined by the synthetic procedure and was set according to the starting material.
ABSTRACT
In the zwitterionic title compound, C(9)H(13)NO(2)S, the pyrrolidine heterocycle adopts an envelope conformation (with the C atom in the 7-position as the flap). The negative charge is delocalized over the two carbonyl groups and the C atom connecting them. The positive charge is located on the S atom. Two inter-molecular C-Hâ¯O inter-actions are observed. The molecular geometry at the S atom is trigonal pyramidal.
ABSTRACT
In the title zwitterionic compound, C(15)H(19)NO(2)S, the six-membered heterocycle adopts a sofa conformation. The negative charge is delocalized along the carbonyl and enolate system on the ring and the positive charge is localized on the S atom. Two inter-molecular C-Hâ¯O inter-actions help to establish the packing.
ABSTRACT
In the title compound, C(21)H(26)N(2)O(3), the morpholine ring has a chair conformation and the dihedral angle between the two phenyl rings is 59.0â (3)°. The crystal packing is stabilized by inter-molecular O-Hâ¯O hydrogen bonds, generating a ribbon structure along the a axis. An intra-molecular N-Hâ¯O contact is also present.