Recent advances in catalytic enantioselective Michael additions

Citation
N. Krause et A. Hoffmann-roder, Recent advances in catalytic enantioselective Michael additions, SYNTHESIS-S, (2), 2001, pp. 171-196
Citations number
193
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
2
Year of publication
2001
Pages
171 - 196
Database
ISI
SICI code
0039-7881(200102):2<171:RAICEM>2.0.ZU;2-D
Abstract
This review summarizes the tremendous achievements in the field of catalyti c enantioselective Michael additions over the last few years. An impressive number of efficient catalytic systems has been established which are compl ementary to each other with respect to applicable Michael accepters and don ors. Copper phosphorus amidites, phosphites and phosphonates are the cataly sts of choice for the highly enantioselective transfer of (functionalized o r unfunctionalized) alkyl groups to cyclic and linear enones. For the corre sponding arylations and alkenylations, however, Rhodium-BINAP catalysts are superior. Remarkably, efficient catalytic systems for Michael additions of malonates and other soft nucleophiles include copper(II) bisoxazolines and heterobimetal complexes. Very recently, even metal-free catalysts (e.g., a lkaloids and peptides) are gaining importance for enantioselective Michael additions. Several applications of these catalysts in natural product synth eses document the high standard now reached in this field.