205526-45-0Relevant articles and documents
Stereocontrolled addition of grignard reagents to chiral 1,3-oxazolidines having N-methoxybenzyl groups : Effect of N-substituent in diastereoselectivity
Yamauchi, Takayasu,Takahashi, Hiroshi,Higashiyama, Kimio
, p. 1813 - 1823 (2007/10/03)
Chiral 1,3-oxazolidines having various N-methoxybenzyl groups were synthesized from (R)-phenylglycinol in three steps. The reactions of chiral 1,3-oxazolidines with Grignard reagents proceeded gently to give the corresponding chiral amines in quantitative yield and high diastereoselectivity. The best results regarding diastereoselectivity were achieved using a chiral 1,3-oxazolidine having N-2,4,6-trimethoxybenzyl moiety. These nitrogen functional groups could be easily removed from the chiral amines using TFA.
Facile diastereoselective reactions of chiral 1,3-oxazolidines with grignard reagents; asymmetric syntheses of 2-substituted and 2,6-disubstituted piperidines
Poerwono, Hadi,Higashiyama, Kimio,Yamauchi, Takayasu,Takahashi, Hiroshi
, p. 385 - 400 (2007/10/03)
(S)- and (R)-2-Phenylpiperidines, (S)- and (R)-2-methylpiperidines, meso- and (2R, 6R)-2,6-diphenylpiperidines, and meso- and (25, 65)-2,6-dimethylpiperidines were synthesized asymmetrically starting from the diastereoselective addition of Grignard reagents to chiral 1,3-oxazolidines, converting of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives as pivotal intermediates.