Desymmetrization of meso-Cyclic Imides via Enantioselective Monohydrogenation

Desymmetrization of meso-Cyclic Imides via Enantioselective Monohydrogenation

meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88−97% ee using trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup- and chemoselectivity, and it is a desymmetrization reacti...

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Veröffentlicht in:Journal of the American Chemical Society 2010-09, Vol.132 (37), p.12832-12834
Hauptverfasser: Takebayashi, Satoshi, John, Jeremy M, Bergens, Steven H
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Hydrogenation
Imides - chemistry
Stereoisomerism
Substrate Specificity
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Zusammenfassung:meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88−97% ee using trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup- and chemoselectivity, and it is a desymmetrization reaction, forming up to five stereogenic centers in one reaction. Conversion of a hydroxy lactam into the corresponding iminium ion followed by addition of indene extended the number of stereogenic centers from 5 to 7.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja105783u