123751-27-9Relevant academic research and scientific papers
Asymmetric Induction in the Wittig-Still Rearrangement of Ethers Containing an Allylic Stereocenter - Diastereocontrol by Allylic Nitrogen
Priebke, Henning,Brueckner, Reinhard,Harms, Klaus
, p. 555 - 564 (2007/10/02)
The stereochemistry of Wittig-Still rearrangements under the influence of an allylic stereogenic center attached by Bn2N or RNBoc groups is studied.Rearrangements are subject to stereocontrol through asymmetric induction.Stannylated allyl ethers 13 with Z double bonds give syn-configuration amino alcohols 15 exclusively (ds >95:99.8:0.2).Stannanes of E configuration 14 lead to 15 less selectively (syn:anti = 46:54 - 92:8).X-ray structural data are provided for amino alcohols syn-15b and for the bis(carbamate) 17.
