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2‐(2,3‐Dihydro‐1 H ‐indol‐3‐yl)ethanol: Synthesis, separation of enantiomers, and assignment of absolute stereochemistry by X‐ray structure analysis
Author(s) -
Frydenvang Karla,
Bech Sommer Michael,
Heckmann Dieter,
Nielsen Ole,
BangAndersen Benny
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10313
Subject(s) - chemistry , enantiomer , chirality (physics) , ethanol , absolute configuration , stereochemistry , resolution (logic) , chiral column chromatography , catalysis , organic chemistry , chiral symmetry , physics , quantum mechanics , artificial intelligence , computer science , nambu–jona lasinio model , quark
The first direct resolution of racemic 2‐(2,3‐dihydro‐l H ‐indol‐3‐yl)ethanol—prepared by catalytic hydrogenation of 2‐(l H ‐indol‐3‐yl)ethanol—has been accomplished by chiral simulated moving bed (SMB) chromatography. The single enantiomers were isolated as their dihydrogen phosphate salts. Single‐crystal X‐ray analyses were successful, revealing that the (+)‐enantiomer of 2‐(2,3‐dihydro‐l H‐ indol‐3‐yl)ethanol has the ( S ) configuration. Chirality 16:126–130, 2004. © 2004 Wiley‐Liss, Inc.