256509-00-9

Upstream product

• 105-36-2 ethyl bromoacetate 
• 256508-94-8 (-)-(1S,2R,6R,7R)-N-butanoyl-3,4-thiazatricyclo[5.2.1.0^2,6]deca-8-ene-3,3-dioxide 
• 197080-12-9 (1S,2R,6R,7R)-3-Thia-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene 3,3-dioxide 
• 645-45-4 hydrocinnamic acid chloride 

Downstream Products

• 281214-25-3 (R)-2-benzyl-butan-1,4-diol 

Relevant academic research and scientific papers

Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries

The use of enantiomerically pure sultams (+)-1 and (-)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic α- bromopropanoate or α-bromobutanoate, the enolates of the corresponding N- acyl sultam underwent highly diastereoselective alkylations to afford products with a complete absolute control of two contiguous chiral centres.