308279-01-8Relevant academic research and scientific papers
[2+2] Cycloaddition of chlorosulfonyl isocyanate to allenyl-sugar ethers
Lysek, Robert,Furman, Bartlomiej,Kaluza, Zbigniew,Frelek, Jadwiga,Suwinska, Kinga,Urbanczyk-Lipkowska, Zofia,Chmielewski, Marek
, p. 3131 - 3150 (2007/10/03)
The direction and magnitude of asymmetric induction in the [2+2] cycloaddition of chlorosulfonyl isocyanate to 3-O-allenyl-α-D-xylofuranoses was investigated. It is shown that gem terminal dimethylallenes react more readily than methyl free congeners. The configuration of adducts was established by X-ray and CD-spectroscopy of alkylidene cephams. A stereochemical model of the transition state for the [2+2] cycloaddition of chlorosulfonyl isocyanate and allenyl ethers is proposed, based on the lowest energy conformation of the cumulene. Copyright (C) 2000 Elsevier Science Ltd.
