ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Radical addition to 2-cyclohexyl-5-methylidene-6-methyl-1,3-dioxan-4-one (2) affords stereoselectively 5,6-trans-products trans-3. The size of the radical has no influence on the selectivity. These trans-acetals are converted into threo-3-hydroxy-butanoates 4. Methyl 2-methylidene-3-[(tert-butyl)diphenylsilyloxy]butanoate (5), treated under the same conditions, leads mainly to the erythro-isomer of 4 after deprotection. An influence of the steric bulkyness of the radical is observed. The stereochemical course of the reactions is discussed.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19910740722
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