ChemInform Abstract: Chemoselective Conjugate Reduction of α,β-Unsaturated Esters and Lactones Under Mild Conditions.

A K2CO3-catalyzed one-pot protocol involving sequential C–C bond formation and cleavage of aromatic β-diketones with α,β-unsaturated esters is developed to obtain 1,5-ketoesters, proceeding smoothly under mild conditions in up to 98% isolated yield.

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Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.16.50 ◽

2020 ◽

Vol 16 ◽

pp. 537-543

Author(s):

Shohei Mimura ◽

Sho Mizushima ◽

Yohei Shimizu ◽

Masaya Sawamura

Keyword(s):

Critical Role ◽

Enantiomeric Excess ◽

Carbene Ligands ◽

Unsaturated Esters ◽

Conjugate Reduction ◽

Phenol Moiety

A chiral phenol–NHC ligand enabled the copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters. The phenol moiety of the chiral NHC ligand played a critical role in producing the enantiomerically enriched products. The catalyst worked well for various (Z)-isomer substrates. Opposite enantiomers were obtained from (Z)- and (E)-isomers, with a higher enantiomeric excess from the (Z)-isomer.

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Asymmetric Conjugate Reduction of ?,?-Unsaturated Esters with Chiral Rhodium(bisoxazolinylphenyl) Catalysts.

ChemInform ◽

10.1002/chin.200517091 ◽

2005 ◽

Vol 36 (17) ◽

Author(s):

Yasunori Tsuchiya ◽

Yoshinori Kanazawa ◽

Takushi Shiomi ◽

Kazuki Kobayashi ◽

Hisao Nishiyama

Keyword(s):

Unsaturated Esters ◽

Conjugate Reduction

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ChemInform Abstract: Selective Conjugate Reduction of α,β-Unsaturated Esters and Amides via SmI2-Promoted Electron Transfer Process.

ChemInform ◽

10.1002/chin.199247116 ◽

2010 ◽

Vol 23 (47) ◽

pp. no-no

Author(s):

J. INANAGA ◽

S. SAKAI ◽

Y. HANDA ◽

M. YAMAGUCHI ◽

Y. YOKOYAMA

Keyword(s):

Electron Transfer ◽

Transfer Process ◽

Electron Transfer Process ◽

Unsaturated Esters ◽

Conjugate Reduction

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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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Palladium-catalyzed decarboxylation-carbonylation of allylic carbonates to give β,γ-unsaturated esters under mild conditions

Tetrahedron Letters ◽

10.1016/s0040-4039(00)85793-7 ◽

1982 ◽

Vol 23 (49) ◽

pp. 5189-5190 ◽

Cited By ~ 30

Author(s):

Jiro Tsuji ◽

Koji Sato ◽

Hiroshi Okumoto

Keyword(s):

Unsaturated Esters ◽

Mild Conditions ◽

Palladium Catalyzed

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Notizen: Homogene katalytische Hydrierung ungesättigter Carbonsäureester mit H2PtCl6 + SnCl2 in iso-Butanol / Homogeneous Catalytic Hydrogenation of Unsaturated Carboxylic Acid Esters with H2PtCl6 + SnCl2 in iso-Butanol

Zeitschrift für Naturforschung B ◽

10.1515/znb-1977-0523 ◽

1977 ◽

Vol 32 (5) ◽

pp. 597-598 ◽

Cited By ~ 2

Author(s):

Walter Strohmeier ◽

Luise Weigelt

Keyword(s):

Carboxylic Acid ◽

Catalytic Hydrogenation ◽

Reaction Rates ◽

Homogeneous Hydrogenation ◽

Unsaturated Esters ◽

Mild Conditions ◽

Unsaturated Carboxylic Acid ◽

Acid Esters

The catalytical system, prepared from H2PtCl6 + SnCl2 · 2 H2O and the additives HBr and H2O in iso-butanol is very efficient for homogeneous hydrogenation of unsaturated esters under mild conditions. Reaction rates r up to 40 mMol · 1-1 · min-1 and turnover numbers UZ higher than 1.600 are observed.

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