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- Title
Synthesis of Open-Chain 2,3-Disubstituted 4-nitroketones by Diastereoselective Michael-addition of ( E)-Enamines to ( E)-Nitroolefins. A topological rule for C, C-bond forming processes between prochiral centres. Preliminary communication.
- Authors
Seebach, Dieter; Goliński, Jerzy
- Abstract
The Michael-additions of aliphatic, alicyclic, and arylsubstituted nitroolefins and enamines lead to γ-nitroketones 3 in good chemical and excellent (> 90%) diastereomeric yields (see Table 1). The known threo-configuration of one type of adducts 3 (entries 8, 10, and 11 of Table 1) can be arrived at by assuming the approach 8 of the Michael-acceptor and -donor; the reaction follows a topological rule, which is formulated and which is applicable to such diverse reactions as the diene synthesis, cyclopropanations, carbonyl olefinations and methylenations, aldol- and nitroaldol-type additions, as well as additions of lithium, boron, and chromium derivatives to aldehydes (see 9, 10, 11, and Table 2).
- Publication
Helvetica Chimica Acta, 1981, Vol 64, Issue 5, p1413
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19810640518