724477-72-9Relevant academic research and scientific papers
A new and convenient route to optically active 2-phosphoryl-3-oxo-5-alkyl/- aryltetrahydrofurans and their reactions
Xu, Chengfu,Zhang, Yonghui,Yuan, Chengye
, p. 2253 - 2262 (2007/10/03)
The two enantiomers of 4-hydroxy-2-oxo-4-alkyl/-arylalkyl-phosphonates were prepared chemoenzymatically and converted to chiral 2-phosphoryl-3-oxo-5-alkyl/ -aryl tetrahydrofurans using an intramolecular O-H insertion reaction catalyzed by rhodium(II) acetate. The potential biological activity of the resulting tetrahydrofurans is of much interest. The presence of the β-ketophosphonate skeleton in these heterocycles allowed their use as substrate in the cyclic Horner-Wadsworth-Emmons reaction with aldehydes or ketones furnishing chiral α,β-unsaturated ketones - a new class of building block in organic synthesis. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
