220198-04-9Relevant academic research and scientific papers
The stereochemical course of addition of allyltrimethylsilane to protected L-alaninals and L-serinals in the presence of Lewis acids. Total synthesis of cis-(2R,3S)-3-hydroxyproline
Gryko,Prokopowicz,Jurczak
, p. 1103 - 1113 (2002)
The influence of Lewis acids on the diastereoselectivity of the addition of allyltrimethylsilane to variously protected L-alaninals and L-serinals was investigated and high levels of asymmetric induction were achieved. Stereochemical models for rationalisation of the results obtained are proposed. cis-(2R,3S)-3-Hydroxyproline was synthesised starting from N-Cbz, O-TBS-L-serinal, in which the crucial step involves addition of allyltrimethylsilane to the aldehyde in the presence of SnCl4.
Diastereoselectivity control in the TiCl4-mediated addition reaction of allyltrimethylsilane to N,O-protected (L)-serinals
Jurczak, Janusz,Prokopowicz, Piotr
, p. 9835 - 9838 (2007/10/03)
The TiCl4- and SnCl4-mediated addition reactions of allyltrimethylsilane (1) to protected (L)-serinals (2-5) were studied, and in the case of TiCl4 a large influence of the N- and O-protecting groups on the stereochemical
