15295-29-1Relevant academic research and scientific papers
Alcohol Dehydrogenases and N-Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β-Disubstituted Allylic Alcohols
González-Granda, Sergio,Lavandera, Iván,Gotor-Fernández, Vicente
supporting information, p. 13945 - 13951 (2021/04/22)
The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer–Schuster rearrangement of a series of readily available propargylic alcohols followed by stereoselective bioreduction of the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted allylic alcohols. This cascade involves a gold N-heterocyclic carbene and an enzyme, demonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions. The combination of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2) and a selective alcohol dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led to the synthesis of a series of optically active (E)-4-arylpent-3-en-2-ols in good yields (65–86 %). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives. The use of alcohol dehydrogenases of opposite selectivity led to the production of both allyl alcohol enantiomers (93->99 % ee) for a broad panel of substrates.
Palladium-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with oxygen in aqueous solvent
Li, Jingjie,Tan, Ceheng,Gong, Jianxian,Yang, Zhen
supporting information, p. 5370 - 5373 (2015/01/09)
A one-pot procedure for Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols to secondary allylic alcohols followed by a Pd(TFA)2/neocuproine-catalyzed oxidative reaction to β-disubstituted-α,β-unsaturated kenones was developed. (Chemical Equation Presented).
Addition of arylboronic acids to arylpropargyl alcohols en route to indenes and quinolines
Panteleev, Jane,Huang, Richard Y.,Lui, Erica K. J.,Lautens, Mark
supporting information; experimental part, p. 5314 - 5317 (2011/12/01)
A regio- and stereoselective rhodium-catalyzed synthesis of trisubstituted allylic alcohols is described. The utility of these synthons is demonstrated in a convenient synthesis of indenes and quinolines.
Chemoenzymatic dynamic kinetic resolution of allylic alcohols: A highly enantioselective route to acyloin acetates
Bogar, Krisztian,Vidal, Pilar Hoyos,Alcantara Leon, Andres R.,Baeckvall, Jan-E.
, p. 3401 - 3404 (2008/02/12)
Dynamic kinetic resolution (DKR) of a series of sterically hindered allylic alcohols has been conducted with Candida antarctica lipase B (CALB) and ruthenium catalyst 1. The optically pure allylic acetates obtained were subjected to oxidative cleavage to
Dynamic processes in the copper-catalyzed substitution of chiral allylic acetates lending to loss of chiral information
Norinder, Jakob,Baeckvall, Jan-E.
, p. 4094 - 4102 (2008/02/08)
Copper-catalyzed a-substitution of enantiomerically pure secondary allylic esters with Grignard reagents was studied with the aim to find conditions that give racemic products. It was observed that the degree of chiral transfer is strongly dependent on th
Enantioselective palladium-catalyzed allylic alkylation using E- and Z-vinylogous sulfonates
Evans, Andrew P.,Brandt, Thomas A.
, p. 1563 - 1565 (2008/02/10)
(matrix presented). The E- and Z-vinylogous sulfonates of β-phenylcinnamyl alcohol derivatives 1 and 2 undergo rapid and enantioselective palladium-catalyzed allylic alkylation (≥90% ee) with the palladium complex of the phosphino-1,3-oxazine 3 and sodium
Enantioselective Synthesis of Succinic Acids and γ-Lactones via Palladium Catalysed Allylic Substitution Reactions
Dawson, Graham J.,Williams, Jonathan M. J.,Coote, Steven J.
, p. 2535 - 2546 (2007/10/03)
The palladium catalyzed reaction between non-symmetrical allyl acetates and sodiodimethylmalonate proceeds in high yields and enantioselectivities (up to 99percent ee) using a diphenylphosphinoaryl oxazoline ligand.The so-formed substitution products are transformed into enantiomerically enriched succinic acids and also into enantiomerically enriched γ-lactones.
Me5Cu3Li2: A Reagent for Conjugate Methylation of α,β-Unsaturated Aldehydes
Clive, Derrick L.J.,Farina, Vittorio,Beaulieu, Pierre L.
, p. 2572 - 2582 (2007/10/02)
Me5Cu3Li2, in ether or ether-pentane mixtures, converts α,β-unsaturated aldehydes efficiently into β-methyl aldehydes.In many cases of synthetic interest the amount of 1,2-methylation is negligible, and the reagent is far superior to Me2CuLi for conjugate methylation of enals.The performance of Me5Cu3Li2 is poor in sterically demanding situations, however.Several cuprate species were evaluated but none works as well as Me5Cu3Li2.For example, citral undergoes conjugate methylation with Me5Cu3Li2 in 80percent yield, and the product contains less than 0.5percent of 1,2-adduct.With Me2CuLi the product contains 10percent of 1,2-adduct.
Conjugate Addition of Methyl Groups to αβ-Unsaturated Aldehydes: Use of Me5Cu3Li2
Clive, Derrick L. J.,Farina, Vittorio,Beaulieu, Pierre
, p. 643 - 644 (2007/10/02)
Me5Cu3Li2 converts αβ-unsaturated aldehydes efficiently into β-methyl aldehydes and, unlike Me2CuLi, it usually gives a negligible amount of the 1,2-adduct even when a quaternary carbon is generated in the reaction.
