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Stereoselective intramolecular cyclization to 4‐(hydroxymethyl)‐3‐(1 H ‐indolyl)oxazolidin‐2‐ones
Author(s) -
Chiummiento Lucia,
Funicello Maria,
Tramutola Francesco
Publication year - 2012
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.22003
Subject(s) - glycidol , chemistry , hydroxymethyl , stereoselectivity , yield (engineering) , intramolecular force , chirality (physics) , stereochemistry , optically active , combinatorial chemistry , organic chemistry , catalysis , materials science , chiral symmetry breaking , physics , quantum mechanics , metallurgy , quark , nambu–jona lasinio model
A simple high‐yield three‐steps route to optically active 4‐hydroxymethyl‐3‐(1 H ‐indolyl)oxazolidin‐2‐ones from ( S )‐glycidol is described. The key intermediates ( R )‐oxiran‐2‐ylmethyl 1 H ‐indol‐4/‐5‐ylcarbamates are obtained in high yields from ( S )‐glycidol. These are readily transformed to oxazolidin‐2‐ones, very interesting building blocks in drug synthesis. Chirality, 2012. © 2012 Wiley Periodicals, Inc.