Selective deoxygenation of allylic alcohol: Stereocontrolled synthesis of lavandulol
Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl 2-catalyzed reduction with LiBHEt3. (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the Pb(OAc)4-promoted oxidative ring-opening of (-)-R-carvone. This deoxygenation method is general and selective for allylic alcohols.
Kim, Hee Jin,Su, Liang,Jung, Heejung,Koo, Sangho
p. 2682 - 2685
(2011/06/26)
A convenient triisobutylaluminium (TIBAL)-promoted Johnson-Claisen approach to γ,δ-unsaturated alcohols
Mixed ortho esters derived from allylic alcohols undergo methanol elimination in the presence of triisobutylaluminium (TIBAL) at room temperature to form mixed ketene acetals. TIBAL then promotes immediate Claisen rearrangement of these intermediates, and
Cosgrove, Kelly L.,McGeary, Ross P.
experimental part
p. 1749 - 1752
(2009/12/04)
Dihydrogen reduction of carboxylic esters to alcohols under the catalysis of homogeneous ruthenium complexes: High efficiency and unprecedented chemoselectivity
(Chemical Equation Presented) The missing link: The presence of two N,P bridges in the ruthenium complexes used as catalysts for the title reaction is essential. Esters that contain isolated C=C bonds are reduced to the corresponding unsaturated alcohols in high yields with high chemoselectivity (see example).
Saudan, Lionel A.,Saudan, Christophe M.,Debieux, Catherine,Wyss, Patrick
p. 7473 - 7476
(2008/09/18)
Metal/Ammonia Reduction of Ethers of 3-Decyn-1-ol: Effects of Structure and Conditions on Cleavage and Rearrangement
Reduction of the THP, ethyl, tert-butyl and tert-butyldimethylsilyl (TBDMS) ethers of 3-decyn-1-ol with sodium in ammonia/THF results in extensive hydrogenolysis of the carbon-oxygen bond and concomitant bond migration, producing a mixture of 2- and 3-decenes and a very low yield of the desired (E)-homoallylic ether.Reduction in the presence of 2-methyl-2-propanol led to excellent yields of the desired (E)-3-decenol ethers.The 4- and 5-decyn-1-ol ethers were reduced normally to the (E)-decen-1-ol ethers except in the case of the TBDMS ethers which were cleaved to the (E)-alcohols under some of the reaction conditions.
Doolittle, Robert E.,Patrick, Delrea G.,Heath, Robert H.
p. 5063 - 5066
(2007/10/02)
REGIOSELECTIVE HYDROALUMINATION OF UNSATURATED HYDROCARBONS BY ALKYLALANES CATALYZED BY ZIRCONIUM COMPLEXES
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Dzhemilev, U. M.,Ibragimov, A. G.,Vostrikova, O. S.,Vasil'eva, E. V.,Tolstikov, G. A.
p. 1004 - 1009
(2007/10/02)
"One-Pot" Conversion of Carboxylic Acid Esters and Lactones to Olefinic Compounds
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Boland, Wilhelm,Ney, Peter,Jaenicke, Lothar
p. 1015 - 1017
(2007/10/02)
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