N-Tosyl-L-Prolyl Chloride置于sodium Hydroxide,三乙胺体系中,用 四氢呋喃,二氯甲烷 作为反应溶剂,化学反应 24.5H,反应生成 1-(甲苯-4-磺酰基)-吡咯烷-2-羧酸
参考文献:Preparation Of Both Enantiomers Of 1-Allyl-1,2,3,4-Tetrahydro-β-Carboline Using Allyltin Reagents And A Chiral Auxiliary Derived From L-Proline
标题:Preparation Of Both Enantiomers Of 1-Allyl-1,2,3,4-Tetrahydro-β-Carboline Using Allyltin Reagents And A Chiral Auxiliary Derived From L-Proline
摘要:Beta-Carboline,Which Had An Acyl Group Derived From L-Proline At The 9-Position,Reacted With Allyltributyltin And 2,2,2-Trichloroethyl Chloroformate,To Afford An 1-Allyl-1,2-Dihydro-Beta-Carboline Derivative In A Diastereo Selective Manner. The Chiral Acyl Group At N-9 Was Readily Eliminated By Aqueous Alkali To Give A Corresponding Carboxylic Acid. The Formed 1-Allyl-1,2-Dihydro-Beta-Carboline Was Transformed Via Two Reduction Steps To 1-Alkyl-1,2,3,4-Tetrahydro-Beta-Carboline In High Ee. When The Allylation Was Carried Out Using Tetraallyltin Instead Of Allyltributyltin,The Stereoselectivity Was Reversed,And The Antipode Of The Allyl Adduct Was Obtained In High Yield And Ee In The Presence Of Tin(Iv) Tetraiodide. Thus,It Was Found That Both Enantiomers Of 1-Allyl-Beta-Carboline Were Obtained In Good Enantioselectivities By The Use Of The Same Chiral Auxiliary. (C) 2001 Elsevier Science Ltd. All Rights Reserved.
DOI:10.1016/s0040-4020(01)00684-6