297168-53-7Relevant academic research and scientific papers
Asymmetric lithiation of an allyl carbamate induced by a complexing remote chiral substituent
Heimbach, Dirk K.,Fr?hlich, Roland,Wibbeling, Birgit,Hoppe, Dieter
, p. 950 - 954 (2007/10/03)
The stereohomogeneous (δ-arenesulfonyloxazolidine)-substituted allyl carbamate 7, after lithiation under several conditions, forms the lithium compound 8 with high diastereoselectivity (dr > 97: 3). 8 is trapped with a number of electrophiles to give the diastereo- and enantiomerically enriched α- and γ-substitution products. Evidence is contributed for: i) 8 is configurationally unstable and the relative configuration is thermodynamically controlled by chelation with the chiral auxiliary, ii) substitution in the α-position proceeds with inversion of the configuration.
