Journal of Organic Chemistry p. 4397 - 4403 (1982)
Update date:2022-09-26
Topics:
DeShong, Philip
Dicken, C. Michael
Staib, Ronald R.
Freyer, Alan J.
Weinreb, Steven M.
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).
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Doi:10.1007/BF00568939
(1982)Doi:10.1023/B:RUCB.0000035654.60768.fb
(2004)Doi:10.1016/S0040-4039(00)87444-4
(1982)Doi:10.1039/b413017k
(2004)Doi:10.1021/om0493661
(2005)Doi:10.1023/B:RJAC.0000038812.89494.22
(2004)
