127221-89-0Relevant academic research and scientific papers
(S)-(-)-1-Amino-2-(siloxymethyl)pyrrolidines: Novel and Efficient Reagents for Chromatographic Resolution of α-Substituted Aldehydes
Enders, Dieter,Mies, Wolfgang
, p. 1221 - 1223 (1984)
A new aldehyde resolution technique based on the chromatographic seperation (preparative h.p.l.c.) of their epimeric (S)-1-amino-2-(siloxymethyl)pyrrolidine (SASP)-hydrazones is described.
Organocerium additions to proline-derived hydrazones: Synthesis of enantiomerically enriched amines
Denmark, Scott E.,Edwards, James P.,Weber, Theodor,Piotrowski, David W.
experimental part, p. 1278 - 1302 (2010/11/02)
The addition of organocerium reagents (from both organolithium and organomagnesium precursors) to chiral aldehyde hydrazones prepared from 1-aminoproline derivatives has been studied. The additions proceed in good yield and high diastereoselectivity and with good nucleophile (Me, n-Bu, i-Pr, t-Bu, Ph, etc.) and substrate scope (alkyl, alkenyl and aryl). The resulting hydrazines can be converted to amines by N-N bond cleavage through hydrogenolysis (Raney nickel) or by acylation and cleavage with Li/NH 3. The influence of the side chain on the diastereoselectivity was investigated through variation of the substituents to include more coordinating atoms (oxygen and nitrogen) as well as the removal of coordinating atoms. The SAMEMP auxiliary bearing a 2-methoxyethoxymethyl group gave the highest diastereoselectivities. Remarkably, auxiliaries bearing simple methyl and isobutyl substituents gave high selectivities as well. Hypotheses for the origin of the selectivity are presented.
A highly enantioselective, moderately anti-selective aldol reaction using a novel hydrazone moiety as stereo director
McGlacken, Gerard P.,Breeden, Simon W.
, p. 3615 - 3618 (2007/10/03)
The use of novel hydrazones as stereo directors with a view to develop a highly enantioselective, anti-diastereoselective aldol addition procedure has been investigated. A number of proline-derived hydrazones were produced and their effectiveness in direc
Synthesis and conformational behaviour of 2-phenylperhydropyrrolo[1,2-4][1,3,4]oxadiazine and 2-phenylperhydropyrido[1,2-d][1,3,4]oxadiazine; new heterocyclic ring systems
Rosling, Ari,Fueloep, Ferenc,Sillanpaeae, Reijo,Mattinen, Jorma
, p. 95 - 106 (2007/10/03)
Hydrazino alcohols, 1-amino-2-hydroxymethylpyrrolidine (1) and 1-amino-2-hydroxymethylpiperidine (2), were synthesized and subsequently ring closured with ethyl benzimidate to the title compounds (7) and (8), which have new ring systems. Variabletemperature 1H nmr measurements, supported by X-ray analysis, indicated that pyrrolo[1,2-d][1,3,4]oxadiazine (7) exists exclusively in a cis-fused conformation (in CDCl3 at room temperature), whereas pyrido[1,2-d][1,3,4]oxadiazine (8) adopts a trans-fused conformation.
