A Convenient Synthesis of (R)- and (S)-2-Anilinomethylpyrrolidines

Stereospecific Migration of P from N to Csp2: Ring-Expansion Reaction of Chiral Diazaphospholidine Oxides

“…The molecular structure of 2, [16] determined by X-ray diffraction, is unusual and interesting. Figure 1 shows an ORTEP [17] plot of the central cluster structure.…”

“…[14,15] Extension of this reaction to phenyldiazaphospholidine oxides compounds as substrates led to remarkable results (Scheme 2). Precursors 9 were readily synthesized by a substitution reaction between phenylphosphonic dichloride ) and (S)-(anilinomethyl)pyrrolidine (8) [16] in THF at 0 8C; a separable mixture of anti-9 and syn-9 in a 50/50 diastereomeric ratio was formed. Subsequent treatment of each pure diastereomer with eight equivalents of LDA at À 78 8C resulted in the migration of the phosphonyl group from the nitrogen to the ortho aromatic carbon atom to produce anti-10 and syn-10 stereoselectively in 90 and 76 % yield, respectively.…”

Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines

“…We heated 9, which is available in two 40 or four 39 steps from pyroglutamate or proline respectively, with aldehydes 1a and 1b in toluene at reflux for 24 h. The NMR spectrum of the crude reaction mixture showed, surprisingly, only a single diastereoisomer (.90:10 diastereoselectivity) of the imidazolines 10a and 10b, and purification by chromatography on neutral alumina (the imidazolines are somewhat sensitive to chromatography on silica) allowed us to isolate these compounds in 88 -89% yield (Scheme 2). X-ray crystallography ( Fig.…”

Synthesis of novel optically active pyrrolidine‐containing polyaniline: A new heterogeneous organo polymeric‐base catalyst for direct Aldol reaction

“…As far as our knowledge is concerned, synthesis method for the preparation of chiral polyaniline base from chiral monomer is not available in the literature. On the basis of the earlier background investigation on chiral conducting polymers, we became interested in the synthesis of chiral polyaniline base, which is prepared from chiral aniline monomer18 bearing a pyrrolidine moiety with aniline unit. This article explores the synthesis, characterization of novel optically active polyaniline, and its application in Aldol reaction.…”