198027-55-3Relevant academic research and scientific papers
The use of chiral auxiliaries prepared from (-)-β-pinene in stereoselective reduction of β-ketobutyrates
Alencar, Karla G.,Filho, Ubiracir F.,Vasconcellos, Mario L.A.A.,Costa, Paulo R.R.
, p. 455 - 468 (2000)
Chiral auxiliaries previously prepared from (-)-β-pinene (3), alcohols 5a-e and 6, were transformed into β-ketobutyrates 7a-e and 8 respectively. These compounds were stereoselectively reduced by NaBH4 in the presence of additives (MnCl2 or CaCl2), leading to the corresponding β-hydroxy butyrates 10a-e and 11 in good chemical yield and poor to moderate stereoselectivities (de 0%-60%). The configuration at the newly generated stereogenic center in 10a was determined to be S through its transformation into S-(+)-butanediol.
