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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
Author(s) -
Seebach Dieter,
Goliński Jerzy
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640518
Subject(s) - chemistry , michael reaction , aldol reaction , diastereomer , alicyclic compound , adduct , addition reaction , lithium (medication) , enantioselective synthesis , tautomer , nitroaldol reaction , acceptor , chain (unit) , stereochemistry , organic chemistry , catalysis , physics , condensed matter physics , medicine , endocrinology , astronomy
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 ).