(S)-2-chloro-2-fluoroethanoyl isocyanate, a chiral derivative of trichloroacetyl isocyanate
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...
Saved in:
Published in | Chirality (New York, N.Y.) Vol. 15; no. 5; pp. 472 - 478 |
---|---|
Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
New York
Wiley Subscription Services, Inc., A Wiley Company
2003
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | 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 1H NMR spectra revealed that the constitution as well as configuration influences regularly the values of chemical shift difference (Δδ = 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. |
---|---|
Bibliography: | ArticleID:CHIR10231 ark:/67375/WNG-TBTJPPZ5-0 Grant Agency of the Czech Republic - No. 203/01/0116; No. 203/02/0436 istex:90DD2A17F1676F69667EDC4255E5DFDA8048DFFF ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0899-0042 1520-636X |
DOI: | 10.1002/chir.10231 |