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Synthesis of Chiral (Indol‐2‐yl)methanamines and Insight into the Stereochemistry Protecting Effects of the 9‐Phenyl‐9‐fluorenyl Protecting Group
Author(s) -
Lood Christopher S.,
Laine Aino E.,
Högnäsbacka Antonia,
Nieger Martin,
Koskinen Ari M. P.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500391
Subject(s) - chemistry , protecting group , stereochemistry , molecular mechanics , group (periodic table) , molecule , organic chemistry , alkyl
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.