(S)-(-)-Fluorenylethylchloroformate (FLEC); preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines

TETRAHEDRON

卷:75

Article

Amin, Mohammad A.¹  Camerino, Michelle A.¹  Mountford, Simon J.¹  Ma, Xiao¹  Manallack, David T.¹  Chalmers, David K.¹  Wills, Martin²  Thompson, Philip E.¹ 

[1] Monash Univ, Med Chem, Monash Inst Pharmaceut Sci, Fac Pharm & Pharmaceut Sci, Parkville Campus,381 Royal Parade, Parkville, Vic 3052, Australia

[2] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

关键词: Fluorenylethylchoroformate;    1-(9H-Fluoren-9-yl)ethan-1-ol;    Chiral derivatisation;    Asymmetric transfer hydrogenation;    Chiral Fmoc;    Chiral resolution;   

DOI  :  10.1016/j.tet.2019.130591

来源: Elsevier

【 摘 要 】

Fluorenylethylchoroformate (FLEC) is a valuable chiral derivatisation reagent that is used for the resolution of a wide variety of chiral amines. Herein, we describe an improved preparation of (S)-(-)-FLEC using an efficient asymmetric catalytic transfer hydrogenation as the key step. We also demonstrate the application of FLEC as a chiral Fmoc equivalent for chiral resolution, with facile deprotection, of tetrahydroquinaldines, and its capacity for inducing regioselective outcomes in nitration reactions. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

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