209900-57-2Relevant academic research and scientific papers
Synthesis of versatile chiral intermediates by enantioselective conjugate addition of alkenyl Grignard reagents to enamides deriving from (R)-(-)- or (S)-(+)-2-aminobutan-1-ol
Brown, Eric,Deroye, Christelle,Touet, Joel
, p. 1605 - 1614 (1998)
Conjugate addition of but-3-enylmagnesium bromide to the chiral crotonamide (R)-(+)- and (S)-(-)-3, followed by hydrolysis and oxidation, afforded enantiopure (R)-(+)- and (S)-(-)-3-methyladipic acids 8, respectively. Conjugate addition of vinylmagnesium chloride to the chiral crotonamide and cinnamamides (R)-(+)-3-5, followed by hydrolysis, gave the alkenoic acids (S)-12-14, respectively. Iodolactonization of the latter led to the 5-iodomethyllactones (+)-15-17, which were reduced by means of n- Bu3SnH into the trans-disubstituted 5-methyllactones (+)-19-21, respectively. Treatment of the iodomethyllactone (+)-16 with LiMe2Cu or n- Bu2CuLi furnished the trans-5-alkyl-4-phenyllactones (-)-22 or (+)-23.
