1461-10-5Relevant academic research and scientific papers
Baker's yeast mediated enantioselective synthesis of the bisabolane sesquiterpenes curcumene, turmerone, dehydrocurcumene and nuciferal
Fuganti, Claudio,Serra, Stefano,Dulio, Andrea
, p. 279 - 282 (1999)
Fermenting baker's yeast converts the allylic alcohol 6 into enantiomerically pure (S)-(+)-3-(p-tolyl)butan-1-ol 7 which is a useful chiral building block for the synthesis of bisabolane sesquiterpenes. The versatility of this approach is shown in the preparation of (S)-(+)-curcumene, (S)-(+)-turmerone, (S)-(+)-dehydrocurcumene and (E,S)-(+)-nuciferal.
Catalytic Regioselective Isomerization of 2,2-Disubstituted Oxetanes to Homoallylic Alcohols
Cabré, Albert,Lledós, Agustí,Rafael, Sergi,Riera, Antoni,Sciortino, Giuseppe,Ujaque, Gregori,Verdaguer, Xavier
supporting information, p. 7521 - 7527 (2020/03/24)
The selective isomerization of strained heterocyclic compounds is an important tool in organic synthesis. An unprecedented regioselective isomerization of 2,2-disubstituted oxetanes into homoallylic alcohols is described. The use of tris(pentafluorophenyl
Method for synthesizing alkyne through catalytic asymmetric cross coupling (by machine translation)
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, (2020/01/12)
The invention belongs to the field of, asymmetric synthesis, and discloses a method for catalyzing asymmetric cross- coupling to synthesize: an alkyne, and the L method comprises, the following steps, of A: preparing B a cuprous, salt and C a: ligand; preparing a catalyst; adding a base; reacting the compound with the compound with the compound; and reacting the compound with the compound. Of these, one of them, X is selected from the group consisting of, R halogens. 1 Optionally substituted heteroarylsulfonylcyanamide groups selected from the, group consisting, of optionally substituted, phenyl groups In-flight vehicle, R6 Trialkyl silyl groups or alkyl radicals, R2 Cycloalkyl radicals optionally substituted with an, optionally substituted alkyl, (CH radical2 )n R4 Multi,layer chain, n＝0-10,R saw blade4 A group selected, from, the group consisting of phenyl, alkenyl, aralkynyls, noonyloxy,and, noonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylphenyl disiloxy-radicals. R3 A ligand, selected from hydrogen or any of the functional groups, is selected from the group consisting of, hydrogen and any L other functional group. The method, R disclosed by the, A invention has the, advantages of good catalytic, R ’ effect, wide application range. and high catalytic efficiency, and the, method disclosed by the, invention has the. advantages of good catalytic effect, wide application range and high catalytic efficiency. (by machine translation)
Effect of multinuclear copper/aluminum complexes in highly asymmetric conjugate addition of trimethylaluminum to acyclic enones
Endo, Kohei,Hamada, Daisuke,Yakeishi, Sayuri,Shibata, Takanori
supporting information, p. 606 - 610 (2013/02/23)
Al and friends: Asymmetric conjugate addition of Me3Al to β,β-disubstituted α,β-unsaturated ketones in the presence copper and L1 leads to a highly efficient construction of an all-carbon-substituted chiral quaternary center. This result is the first example of an asymmetric conjugate addition of Me3Al to acyclic enones to give a chiral quaternary carbon center with excellent yield and enantioselectivity under mild reaction conditions. Copyright
Catalytic enantioselective β-alkylation of α,β-unsaturated aldehydes by combination of transition-metal- and aminocatalysis: Total synthesis of bisabolane sesquiterpenes
Afewerki, Samson,Breistein, Palle,Pirttil?, Kristian,Deiana, Luca,Dziedzic, Pawel,Ibrahem, Ismail,C?rdova, Armando
supporting information; experimental part, p. 8784 - 8788 (2011/09/15)
Branching out! The first co-catalytic enantioselective (up to 98:2 e.r.) β-alkylation of α,β-unsaturated aldehydes by combination of simple chiral amine and copper catalysts provides β-branched aldehydes in a one-pot protocol (see scheme). The methodology was applied to the short total syntheses of bisabolane sesquiterpenes (S)-(+)-curcumene, (E)-(S)-(+)-3- dehydrocurcumene and (S)-(+)-tumerone.
Catalytic conjugate additions of geminal bis(sulfone)s: Expanding the chemistry of sulfones as simple alkyl anion equivalents
Landa, Aitor,Puente, Angel,Santos, J. Ignacio,Vera, Silvia,Oiarbide, Mikel,Palomo, Claudio
experimental part, p. 11954 - 11962 (2010/05/02)
The value of cyclic gem-bis-(sulfone) 4 as a simple alkyl nucleophile equivalent in catalytic C-C bondforming reactions is demonstrated. The 1,4-type nucleophilic additions of bis-(sulfone) 4 to α,β-unsaturated ketones take place by assistance of catalyti
Total synthesis of (R)- and (S)-turmerone and (7S,9R)-bisacumol by an efficient chemoenzymatic approach
Kamal, Ahmed,Shaheer Malik,Azeeza, Shaik,Bajee, Shaik,Shaik, Ahmad Ali
experimental part, p. 1267 - 1271 (2009/10/17)
An enantioselective synthesis of (R)-, (S)-turmerone and (7S,9R)-bisacumol is described. The enantiomerically pure key intermediates, a substituted butanoate ester and acid are utilized in the synthesis of both enantiomers of turmerone. The lipase catalyzed resolution studies of the acetate of bisacumol have been exploited towards the total synthesis of the naturally occurring cytotoxic sesquiterpene, (7S,9R)-bisacumol with high diastereoselectivity (94% de).
Enantioselective synthesis of (R)- and (S)-curcumene and curcuphenol: an efficient chemoenzymatic route
Kamal, Ahmed,Malik, M. Shaheer,Shaik, Ahmad Ali,Azeeza, Shaik
, p. 2547 - 2553 (2008/03/15)
An efficient enantioselective synthesis of curcumene and curcuphenol is described. The key intermediates, substituted butanoates 7a and 7b and their acids 8a and 8b are obtained in high enantiopurity (>99% ee) by a lipase-catalyzed kinetic resolution proc
Benzothiazines in synthesis. Formal syntheses of (+)-curcumene and (+)-curcuphenol
Harmata, Michael,Hong, Xuechuan,Barnes, Charles L.
, p. 7261 - 7264 (2007/10/03)
A benzothiazine readily available in enantiomerically pure form via a stereoselective, intramolecular Michael addition reaction could be converted to a precursor to (+)-curcuphenol and to (+)-curcumene.
