A Simplified Version of the Phospha-Wittig Synthesis of P=C Double Bonds from Carbonyl Compounds

Synlett ◽  
1990 ◽  
Vol 1990 (03) ◽  
pp. 171-172 ◽  
Author(s):  
Pascal Le Floch ◽  
François Mathey
Keyword(s):  
Carbonyl Compounds ◽  
Double Bonds

scholarly journals n-Butyltriphenylphosphonium Peroxodisulfate (BunPPh3)2S2O8: An Efficient and Inexpensive Reagent for the Cleavage of Carbon–Nitrogen Double Bonds under Non-aqueous and Aprotic Conditions

1999 ◽  
Vol 23 (2) ◽  
pp. 102-103
Author(s):  
Iraj Mohammadpoor-Baltork ◽  
Abdol Reza Hajipour ◽  
Reza Haddadi
Keyword(s):  
Carbonyl Compounds ◽  
Double Bonds

An efficient and convenient conversion of oximes, phenylhydrazones, p-nitrophenylhydrazones and semicarbazones to the corresponding carbonyl compounds with n-butyltriphenylphosphonium peroxodisulfate is reported.

Reduction of conjugate double bonds with trichlorosilane

2000 ◽  
Vol 78 (11) ◽  
pp. 1396-1398 ◽  
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 carbon–carbon 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.

scholarly journals Reduction of carbonyl compounds via hydrosilylation catalyzed by well-defined PNP-Mn(I) hydride complexes

2021 ◽  
Author(s):  
Stefan Weber ◽  
Dina Iebed ◽  
Mathias Glatz ◽  
Karl Kirchner
Keyword(s):  
Carbonyl Compounds ◽  
Hydrogen Donor ◽  
Synthetic Chemistry ◽  
Double Bonds ◽  
Reduction Reactions ◽  
Hydride Complexes ◽  
Unsaturated Compounds ◽  
Aldehydes And Ketones ◽  
Hydrogenation Reactions

AbstractReduction reactions of unsaturated compounds are fundamental transformations in synthetic chemistry. In this context, the reduction of polarized double bonds such as carbonyl or C=C motifs can be achieved by hydrogenation reactions. We describe here a highly chemoselective Mn(I)-based PNP pincer catalyst for the hydrosilylation of aldehydes and ketones employing polymethylhydrosiloxane (PMHS) as inexpensive hydrogen donor. Graphic abstract

Aminolithiation of carbon-carbon double bonds as a powerful tool in organic synthesis

2009 ◽  
Vol 81 (2) ◽  
pp. 247-253 ◽  
Author(s):  
Kiyoshi Tomioka ◽  
Takeo Sakai ◽  
Tokutaro Ogata ◽  
Yasutomo Yamamoto
Keyword(s):  
Carbonyl Compounds ◽  
Chiral Ligand ◽  
Powerful Method ◽  
Double Bonds ◽  
One Pot ◽  
Bond Forming ◽  
Lithium Amides ◽  
Lithium Enolates ◽  
Amination Product

A conjugate amination of α,β-unsaturated carbonyl compounds with lithium amides has become a powerful method of N-C bond-forming reactions. Chiral ligand-controlled asymmetric version of the conjugate amination of enoates was developed for practical bench chemistry, giving the enantioenriched amination product with over 99 % ee. In situ diastereoselective alkylation of resulting lithium enolates allowed us to form vicinal N-C and C-C bonds in a one-pot operation. This protocol enabled us to realize a short-step asymmetric synthesis of otamixaban key intermediate. Treatment of product 3-benzylamino- and 3-allylaminoesters with tert-butyllithium gave five- or seven-membered lactams through [1,2]- or [2,3]-rearrangement of intermediate β-lactams. Isolated C-C double bonds were also found to accept intramolecular aminolithiation affording the corresponding hydroamination products. Chiral lithiophilic ligand-catalyzed reaction gave enantioenriched hydroamination products with high ee. Stereoselective intramolecular aminolithiation of allylaminoalkenes was coupled with subsequent carbolithiation to give doubly cyclized product amines.

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