867367-13-3

Upstream product

• 867367-11-1 ethyl (2E)-4-{benzyl[(2E)-4-chloro-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate 
• 138777-15-8 ethyl 4-{[tert-butyl(dimethyl)silyl]oxy}-3-methyl-2-butenoate 
• 144001-42-3 methyl 2-(benzylamino)-3-hydroxypropanoate 
• 132032-97-4 (2E)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-methyl-2-buten-1-ol 
• 524960-39-2 {[(2E)-4-bromo-2-methyl-2-butenyl]oxy}(tert-butyl)dimethylsilane 

Relevant academic research and scientific papers

Novel approach to the (-)-sparteine-mediated synthesis of kainoids: Total synthesis of (-)-α-kainic acid by (-)-sparteine-mediated deprotonation

We report a new synthesis of kainoids via allyllithium compounds using an intramolecular cycloalkylation as the key step. Preparation of different substituted pyrrolidines was carried out by using carbamates, that react with the chiral base n-BuLi/(-)-sparteine with strong selection between the diastereotopic protons adjacent to the carbamate group in favour for the pro-S proton. (-)-α-Kainic acid was synthetized from D-serine methyl ester hydrochloride, based on a (-)-sparteine-mediated asymmetric deprotonation of an intermediate carbamate that, by stereospecific anti-SN′S E′ intramolecular cycloalkylation, leads to the pyrrolidine ring precursor of (-)-α-kainic acid, in high yield and diastereoselectivity. Related approaches, starting from L-glutamic acid failed. The intermediate pyrrolidine was further transformed to (-)-α-kainic in three steps. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.