ISSN:
0947-6539
Keywords:
benzoic acids
;
carbanions
;
lithiation
;
stannylation
;
stereochemistry
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Configurationally stable, dipole-stabilised benzyllithium compounds (R)-and (S)-1 b, prepared by deprotonation of the corresponding esters with sBuLi in toluene/di-ethyl ether (5:1), reacted with (-)-menthyldimethyltin bromide to afford the stannanes (-)-3 and ( + )-4, respectively. A single-crystal X-ray structure analysis of compound (-)-3 proved that stannylation occurred with inversion of the configuration at the benzylic centre, assuming retention for the deprotonation step. Lithio-destannylation and deuteration with MeOD follow a retentive course.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19970031022