Synthesis of Chiral (Indol‐2‐yl)methanamines and Insight into the Stereochemistry Protecting Effects of the 9‐Phenyl‐9‐fluorenyl Protecting Group. Issue 17 (1st May 2015)

• Record Type: Journal Article
• Authors: Lood, Christopher S.; Laine, Aino E.; Högnäsbacka, Antonia; Nieger, Martin; Koskinen, Ari M. P.
• Is Part Of: European journal of organic chemistry. Issue 17(2015)
• Page Start: 3793
• Page End: 3805
• Publication Date: 2015-05-01
• Subjects: Asymmetric synthesis -- Amino acids -- Chiral pool -- Protecting groups; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500391
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Tetrahydro‐β‐carbolines, a privileged structural feature in natural products and pharmaceutically active compounds, has been the cause for considerable research interest, spanning many decades. Herein is reported the synthesis of the structurally closely related compounds denoted as (indol‐2‐yl)methanamines, in 99 % ee using amino acid starting materials, coupled with a 9‐phenyl‐9‐fluorenyl (Pf) protecting group strategy. Furthermore a conformational study of Pf‐protected α‐amino carbonyl compounds were undertaken by means of DFT refined molecular mechanics calculation, X‐ray crystallography measurements and NMR experiments in order to elucidate the stereochemical protecting properties induced by the Pf group. Abstract : Herein is presented a highly efficient stereospecific synthesis of (indol‐2‐yl)methanamines from amino acids together with a mechanistic study on the stereochemistry protecting effects of the 9‐phenyl‐9‐fluorenyl protecting group with the aid of DFT calculations, NMR and X‐ray crystallography.