57133-41-2Relevant academic research and scientific papers
SYNTHESE D'α-HYDROXY ACIDES OPTIQUEMENT ACTIFS
Boireau, G.,Abenhaim, D.,Deberly, A.,Sabourault, B.
, p. 1259 - 1262 (1982)
The reaction of chiral MAlR3OR' (M=Li, Na, K; R=Me, Et; OR' from R'OH=(-)N-methylephedrine) with C6H5COCO2(-)-menthyl provide a good synthesis of α-alkyl mandelic acids with enantiomeric excess (e.e.) up to 53 percent.Asymmetric induction due to both the chiral centers of the (-)-menthyl group and the OR' group may be invoked to account for the higher stereoselectivity observed in the reaction.
The stereoselective synthesis of 2-aryl-2-hydroxybutanoic acid via menthyl chiral auxiliaries
Xiang, Ji-Ming,Li, Bao-Lin
scheme or table, p. 2015 - 2022 (2010/12/25)
In the presence of titanium(IV) tetraethoxide ((EtO)4Ti), menthyl arylglyoxylates are prepared by transesterification of ethyl arylglyoxylates and natural (-)-(1R,2S,5R)-menthol. Using menthyl as a chiral auxiliary, the corresponding novel (R)-menthyl 2-aryl-2-hydroxybutanoates are synthesized by the addition of Et2Zn with menthyl arylglyoxylates. The structures of the products are characterized by IR and 1H- and 13C-NMR spectroscopy, mass spectrometry, and elemental analysis. The diastereoselectivities are analyzed by HPLC. The addition reactions are completed with good yields and high diastereoisomeric excess (de up to 95%), and, after hydrolysis, the (R)-2-aryl-2-hydroxybutanoic acids are obtained with high optical purities.
SYNTHESE D'α-HYDROXYACIDES OPTIQUEMENT ACTIFS PAR ADDITION D'ORGANOZINCIQUES SUR LE PHENYLGLYOXALATE DE (-) MENTHYLE
Boireau, G.,Deberly, A.,Abenhaim, D.
, p. 5837 - 5844 (2007/10/02)
Organozinc compounds readily obtained in situ from Grignard reagents and solutions of ZnCl2 or ZnBr2 in diethylether or THF add selectively to the keto group of (-) menthyl phenylglyoxalate.A variety of α-substituted mandelic acids o
ADDITION DIASTEREOSELECTIVE D'ORGANOZINCIQUES SUR LE PHENYLGLYOXALATE DE (-) MENTHYLE
Boireau, G.,Deberly, A.,Abenhaim, D.
, p. 2175 - 2176 (2007/10/02)
Organozinc compounds (from Grignard reagents and ZnCl2 or ZnBr2 in diethylether or THF) add selectively to the keto group of (-) menthyl phenylglyoxalate, to give α-substituted (-) menthyl mandelates in high yields and in most cases high levels of asymmet
