ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Variously substituted 4,5-dihydro-5-vinylisoxazoles, obtained by regio- and stereospecific cycloaddition of nitrile oxides to dienes, undergo smooth OsO4-catalyzed cis-hydroxylation to give amino-polyol precursors. The reaction is ‘anti’-selective, the diastereoisomeric ratios ranging from 73:27 up to ≥ 99:1. Thus, the cycloaddition/osmylation sequence allows the control of the relative configuration of up to four contiguous asymmetric centers. A sulfoxide-mediated approach to enantiomerically pure compounds is also described.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680518
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