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α,β‐Unsaturated Carbonyl Compounds with Sterically Protected Carbonyl Groups—Enforced a 3 versus a 1 Reactivity
Author(s) -
Seebach Dieter,
Locher Rita
Publication year - 1979
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197909571
Subject(s) - steric effects , reactivity (psychology) , carbonyl group , chemistry , adduct , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology
A shift in the reactivity of α,β‐unsaturated carbonyl compounds can be accomplished by steric protection of the carbonyl group. Thus (1) reacts with organolithium exclusively at C‐3 to give Michael adducts (2) which can be cleaved to form carboxylic acid derivatives.