Premium
(S)‐2‐chloro‐2‐fluoroethanoyl isocyanate, a chiral derivative of trichloroacetyl isocyanate
Author(s) -
Vodička Petr,
Streinz Ludvík,
Koutek Bohumír,
Buděšínský Miloš,
Ondrácek Jan,
Císařová Ivana
Publication year - 2003
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.10231
Subject(s) - chemistry , isocyanate , diastereomer , molecule , reactivity (psychology) , stereochemistry , alkyl , chemical shift , derivative (finance) , medicinal chemistry , organic chemistry , polyurethane , medicine , alternative medicine , pathology , financial economics , economics
Carbamate diastereomers 3b–18b were prepared from easily accessible ( S )‐2‐chloro‐2‐fluoroethanoyl isocyanate ( 1 ) and various secondary chiral alcohols. Compound 1 as a chiral analog of trichloroacetyl isocyanate undergoes the reaction with alcohols very fast, thus blocking the hydroxyl group for the purposes of NMR investigation. Moreover, the correlation of stereochemistry of 3b–18b with their 1 H NMR spectra revealed that the constitution as well as configuration influences regularly the values of chemical shift difference (Δ δ = δ ( R ) – δ ( S )) except for those diastereomers bearing simple alkyl groups in the molecule. Spectral as well as crystallographic data manifest the predominant planar conformation of the central part of the molecule. Due to the good accessibility and high reactivity in particular, the acylisocyanate 1 might be considered, to some extent, an alternative for TAI giving additional information on a compound's spatial structure. Chirality 15:472–478, 2003. © 2003 Wiley‐Liss, Inc.