83077-22-9Relevant academic research and scientific papers
Determination of Configuration and Conformation of Isoxazolidines by Nuclear Overhauser Effect Difference Spectroscopy
DeShong, Philip,Dicken, C. Michael,Staib, Ronald R.,Freyer, Alan J.,Weinreb, Steven M.
, p. 4397 - 4403 (1982)
The configurations of isoxazolidines 2, 3, 5, 7, and 10-12 have been assigned by analysis of NMR coupling constants and by nuclear Overhauser effect difference spectroscopy (NOEDS).The preferred solution conformations of isoxazolidines 3 and 5 were determined to be as in 3A/5A.It is proposed that these conformations are adopted to take advantage of the anomeric effect and to alleviate the unfavorable stereoelectronic lone pair-lone pair interaction in the N-O portion of the molecule (gauche effect).
