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Identification of Chiral cis‐ and trans‐ 2‐Stannyloxazolidines by Their NMR Spectra and Solid‐State Structures
Author(s) -
Cintrat JeanChristophe,
LéatCrest Véronique,
Parrain JeanLuc,
Grognec Erwan Le,
Beaudet Isabelle,
Toupet Loïc,
Quintard JeanPaul
Publication year - 2004
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.200400203
Subject(s) - chemistry , oxazolidine , solid state , nmr spectra database , ring (chemistry) , stereochemistry , computational chemistry , crystallography , chemical shift , spectral line , torsion (gastropod) , organic chemistry , physics , astronomy , medicine , surgery
The assignment of cis and trans configurations in N ‐protected 4‐substituted 2‐tributylstannyl‐1,3‐oxazolidines by NMR has been achieved through the use of extrapolations of Karplus−Kitching‐type relationships for 3 J ( 119 Sn−C−Z− 13 C) to establish the shape of the oxazolidine ring. Examination of 3 J (H,H) allowed the determination of torsion angles for the substituents on C 4 and C 5 , discrimination being completed by comparison of the H 2 chemical shifts, together with the 2 J (Sn−C−H 2 ) values. The validity of the method was subsequently corroborated by comparison of the results obtained for the liquid phase with those obtained from radiocrystallographic structures of triphenylstannyl analogues or DFT calculations on trimethylstannyl analogues. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)