360767-46-0Relevant academic research and scientific papers
The first enantioselective synthesis of (S)-5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine: A key intermediate for the preparation of SIB-1508Y
Felpin, Francois-Xavier,Vo-Thanh, Giang,Villieras, Jean,Lebreton, Jacques
, p. 1121 - 1124 (2001)
The first enantioselective synthesis of (S)-5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine is described via intramolecular hydroboration-cycloalkylation of an azido-olefin intermediate. The chiral homoallylic alcohol was efficiently synthesized by enantioselective reduction of the corresponding ketone using (+)-diisopinocamphenylchloroborane as the key reaction. The total synthesis of (S)-SIB-1508Y was achieved with an enantiomeric excess (e.e.) of 94% in ten steps and in 18% overall yield from the commercially available 5-bromo-3-pyridinecarboxylic acid.
Enantioselective reduction of heteroaromatic β,γ-unsaturated ketones as an alternative to allylboration of aldehydes. Application: Asymmetric synthesis of SIB-1508Y
Felpin, Fran?ois-Xavier,Bertrand, Marie-Jo,Lebreton, Jacques
, p. 7381 - 7389 (2007/10/03)
Enantioselective reduction of heteroaromatic β,γ-unsaturated ketones was found to be an efficient and convenient alternative to the allylboration of corresponding aldehydes. This new method was used for the formal asymmetric synthesis of SIB-1508Y 2.
