Enantioselective Hydrogenation of the Double Bond of Exocyclic α,β-Unsaturated Carbonyl Compounds Catalyzed by Iridium/H8-BINOL-Derived Phosphine-Oxazoline Complexes

A protocol for the copper-catalyzed oxidative self-coupling of α-amino carbonyl compounds has been developed for the synthesis of tetrasubstituted 1,4-enediones (Z-isomers) in moderate to good yields through the cleavage of four sp3C–H bonds and the simultaneous formation of one C=C double bond in the α-amino carbonyl compound. The strategy has the advantages of using readily available starting materials and of high stereoselectivity.

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Highly Enantioselective Hydrogenation of Exocyclic Double Bond of N-Tosyloxazolidinones Catalyzed by a Neutral Rhodium Complex and Its Synthetic Applications.

ChemInform ◽

10.1002/chin.200701031 ◽

2007 ◽

Vol 38 (1) ◽

Author(s):

Zengming Shen ◽

Xiyan Lu ◽

Aiwen Lei

Keyword(s):

Double Bond ◽

Enantioselective Hydrogenation ◽

Rhodium Complex ◽

Exocyclic Double Bond

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ChemInform Abstract: Catalytic Asymmetric Reductive Amination of Ketones via Highly Enantioselective Hydrogenation of the C=N Double Bond.

ChemInform ◽

10.1002/chin.199433036 ◽

2010 ◽

Vol 25 (33) ◽

pp. no-no

Author(s):

M. J. BURK ◽

J. P. MARTINEZ ◽

J. E. FEASTER ◽

N. COSFORD

Keyword(s):

Double Bond ◽

Reductive Amination ◽

Enantioselective Hydrogenation ◽

Catalytic Asymmetric

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Reaction of lithium dimethylcuprate with (α-allenic carbonyl compounds: A 1,2-addition to the activated carbon—carbon double bond. Direct evidence for an α-cuprio ketone/copper enolate equilibrium

Journal of Organometallic Chemistry ◽

10.1016/s0022-328x(00)90655-7 ◽

1978 ◽

Vol 152 (3) ◽

pp. 359-365 ◽

Cited By ~ 24

Author(s):

Jacques Berlan ◽

Jean Paul Battioni ◽

Karim Koosha

Keyword(s):

Activated Carbon ◽

Double Bond ◽

Carbonyl Compounds ◽

Direct Evidence ◽

Carbon Double Bond

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Reactivity of the double bond in coumarins and related α−β unsaturated carbonyl compounds

Proceedings of the Indian Academy of Sciences - Section A ◽

10.1007/bf03045338 ◽

1936 ◽

Vol 4 (6) ◽

pp. 630-638 ◽

Cited By ~ 3

Author(s):

P. Suryaprakasa Rao ◽

T. R. Seshadri

Keyword(s):

Double Bond ◽

Carbonyl Compounds

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Heterogeneous Enantioselective Hydrogenation and Dihydroxylation of Carbon Carbon Double Bond Mediated by Transition Metal Asymmetric Catalysts

Chiral Reactions in Heterogeneous Catalysis ◽

10.1007/978-1-4615-1909-6_18 ◽

1995 ◽

pp. 155-176 ◽

Cited By ~ 3

Author(s):

Dario Pini ◽

Antonella Petri ◽

Alberto Mastantuono ◽

Piero Salvadori

Keyword(s):

Double Bond ◽

Transition Metal ◽

Enantioselective Hydrogenation ◽

Asymmetric Catalysts ◽

Carbon Double Bond

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ChemInform Abstract: CUMULATED DOUBLE BOND SYSTEMS AS LIGANDS. VI. CARBONYL COMPOUNDS OF CHROMIUM(0), MOLYBDENUM(0), AND TUNGSTEN(0) CONTAINING THIODIIMINE LIGANDS. MECHANISM OF THE FLUXIONAL PROCESS AND RESONANCE RAMAN RESULTS

Chemischer Informationsdienst ◽

10.1002/chin.197735311 ◽

1977 ◽

Vol 8 (35) ◽

pp. no-no

Author(s):

R. MEIJ ◽

T. A. M. KAANDORP ◽

D. J. STUFKENS ◽

K. VRIEZE

Keyword(s):

Double Bond ◽

Carbonyl Compounds ◽

Resonance Raman ◽

And Tungsten

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ChemInform Abstract: Phosphorus-Carbon Double Bond Systems by Condensation of Primary Phosphines with Carbonyl Compounds? The Development of a New Synthesis Concept for Preparation of Substituted Phosphaalkenes

ChemInform ◽

10.1002/chin.199201317 ◽

2010 ◽

Vol 23 (1) ◽

pp. no-no

Author(s):

H. OEHME

Keyword(s):

Double Bond ◽

Carbonyl Compounds ◽

Carbon Double Bond ◽

New Synthesis

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Reduction of conjugate double bonds with trichlorosilane

Canadian Journal of Chemistry ◽

10.1139/v99-238 ◽

2000 ◽

Vol 78 (11) ◽

pp. 1396-1398 ◽

Cited By ~ 7

Author(s):

Moni Chauhan ◽

Philip Boudjouk

Keyword(s):

Double Bond ◽

Carbonyl Compounds ◽

Double Bonds ◽

Cyclic Ketones ◽

Unsaturated Esters ◽

Mild Conditions ◽

Carbon Double Bond

A variety of α,β-unsaturated esters and cyclic ketones underwent smooth reduction of the carboncarbon double bond with a combination of inexpensive and readily available trichlorosilane and CoCl2. The reactions are performed under very mild conditions and products are obtained in high yields.Key words: reduction, carbonyl compounds, trichlorosilane, ketones, chemoselectivity.

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