1462-73-3Relevant articles and documents
A short enantioselective synthesis of ephedrine, amphetamine and their analogues via two stereocentered Co(III)-catalyzed hydrolytic kinetic resolution of racemic syn-benzyloxy epoxide
Lalwani, Komal G.,Sudalai, Arumugam
, p. 6488 - 6490 (2015/11/16)
An efficient route for the synthesis of 6 drugs belonging to phenethylamine and amphetamine classes in excellent overall yields and high optical purity has been described. The strategy involves introduction of stereogenic centers by means of two-stereocentered Co(III)-catalyzed hydrolytic kinetic resolution (HKR) of racemic syn-benzyloxy epoxide followed by Pd-catalyzed regioselective cationic hydrogenation of amino alcohols as the key reactions.
Resolution of chiral aliphatic and arylalkyl amines using immobilized Candida antarctica lipase and isolation of their R- and S-enantiomers
Davis,Durden
, p. 569 - 578 (2007/10/03)
The resolution of chiral aliphatic and arylalkyl amines in high enantiomeric excess (up to 97.5% ee for the R-enantiomers and up to 99.9% ee for the S-enantiomers) and good yield (50-80%) using immobilized Candida antarctica lipase and ethyl acetate as acyl donor has been demonstrated. A second resolution on the Ramine increased the enantiomeric excess to more than 99.5% (up to 99.9%).
Asymmetric synthesis of chiral amines by highly diastereoselective 1,2- additions of organometallic reagents to N-tert-butanesulfinyl imines
Cogan, Derek A.,Liu, Guangcheng,Ellman, Jonathan
, p. 8883 - 8904 (2007/10/03)
High yielding and highly diastereoselective methods for 1,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) and N-tert- butanesulfinyl kerimines (3) are described. The additions of alkyl, aryl, alkenyl, and allyl carbanions to a diverse set of imines with different steric and electronic properties are demonstrated. Acidic methanolysis of the sulfinamide products (4 and 6) delivers highly enantioenriched α-branched and α,α-dibranched amines. Since a broad range of sulfinyl imines are easily accessible from aldehydes and ketones, a wide variety of enantioentriched amines may be prepared.