Four racemic tetrahydroisoquinolines(RS)-(±)-1-4 were prepared from homoveratrylamine via amidation,Bischler-Napieralski reaction and the subsequent reduction.The enantiomerically pure tetrahydroisoquinolines(S)-...Four racemic tetrahydroisoquinolines(RS)-(±)-1-4 were prepared from homoveratrylamine via amidation,Bischler-Napieralski reaction and the subsequent reduction.The enantiomerically pure tetrahydroisoquinolines(S)-(−)-norcryptostyline Ⅰ[(S)-(−)-1],(S)-(−)-norcryptostyline Ⅱ[(S)-(−)-2],(R)-(+)-salsolidine[(R)-(+)-3]and(S)-(−)-norlaudanosine[(S)-(−)-4]were then obtained in 45%,40%,41%and 38%yields,respectively,via resolution of the racemic compounds(RS)-(±)-1-4 with half equivalent of chiral acids.In addition,the enantiomerically enriched compounds(R)-(+)-1,(R)-(+)-2,(S)-(−)-3 and(R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.展开更多
基金We thank the National Natural Science Foundation of China(No.20972048)for the financial support of this work.
文摘Four racemic tetrahydroisoquinolines(RS)-(±)-1-4 were prepared from homoveratrylamine via amidation,Bischler-Napieralski reaction and the subsequent reduction.The enantiomerically pure tetrahydroisoquinolines(S)-(−)-norcryptostyline Ⅰ[(S)-(−)-1],(S)-(−)-norcryptostyline Ⅱ[(S)-(−)-2],(R)-(+)-salsolidine[(R)-(+)-3]and(S)-(−)-norlaudanosine[(S)-(−)-4]were then obtained in 45%,40%,41%and 38%yields,respectively,via resolution of the racemic compounds(RS)-(±)-1-4 with half equivalent of chiral acids.In addition,the enantiomerically enriched compounds(R)-(+)-1,(R)-(+)-2,(S)-(−)-3 and(R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.
