220198-02-7

Upstream product

• 209266-23-9 N-benzyl-N-benzyloxycarbonyl-O-benzyloxymethyl-L-serinal 
• 762-72-1 allyl-trimethyl-silane 
• 3587-60-8 Benzyloxymethyl chloride 
• 123411-86-9 (1S,2S)-(2-hydroxy-1-hydroxymethylpent-4-enyl)carbamic acid benzyl ester 
• 154161-00-9 (1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-hydroxypent-4-enyl]carbamic acid benzyl ester 
• 154161-01-0 [(2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester 

Relevant 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

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

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