82167-79-1Relevant academic research and scientific papers
Lewis Base–Br?nsted Acid–Enzyme Catalysis in Enantioselective Multistep One-Pot Syntheses
Giesler, Markus,Guder, Marian,Hartmann, Laura,Mantel, Marvin,Pietruszka, J?rg,Rüthlein, Elisabeth
supporting information, p. 16700 - 16706 (2021/05/07)
Establishing one-pot, multi-step protocols combining different types of catalysts is one important goal for increasing efficiency in modern organic synthesis. In particular, the high potential of biocatalysts still needs to be harvested. Based on an in-depth mechanistic investigation of a new organocatalytic protocol employing two catalysts {1,4-diazabicyclo[2.2.2]octane (DABCO); benzoic acid (BzOH)}, a sequence was established providing starting materials for enzymatic refinement (ene reductase; alcohol dehydrogenase): A gram-scale access to a variety of enantiopure key building blocks for natural product syntheses was enabled utilizing up to six catalytic steps within the same reaction vessel.
(3R)-2-iodo-4-benzyloxy-3-methyl-1-ene compound as well as preparation method and application thereof
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Paragraph 0046; 0047; 0048, (2019/08/02)
The invention provides a (3R)-2-iodo-4-benzyloxy-3-methyl-1-ene compound as well as a preparation method and an application thereof, more particularly relates to a novel compound ERP-2 as well as a preparation method and an application thereof, also provi
Simple organocatalysts in multi-step reactions: An efficient one-pot Morita-Baylis-Hillman-type α-hydroxymethylation of vinyl ketones followed by the convenient, temperature-controlled one-pot etherification using alcohols
Mantel, Marvin,Guder, Marian,Pietruszka, J?rg
supporting information, p. 5442 - 5450 (2018/05/25)
1,4-Diazabicyclo[2.2.2]octane (DABCO) was utilized as versatile catalyst in a one-pot synthesis: First, for the preparation of alcoholic formaldehyde solutions from para-formaldehyde catalysed by using low loadings of inexpensive DABCO. Second, for the fast α-hydroxymethylation of alkylic and aromatic vinyl ketones in high yields. In a third step, the same catalyst can be used for an optional, temperature controlled in situ etherification of the Morita-Baylis-Hillman product with various alcohols on a multi-gram scale in moderate to good overall yields and high purities. Furthermore, an application of the ether in the enantioselective synthesis of a common building block for total synthesis is shown, thus providing a gram-scale access from inexpensive bulk chemicals.
Synthesis of optically active bifunctional building blocks through enantioselective copper-catalyzed allylic alkylation using Grignard reagents
Van Zijl, Anthoni W.,Lopez, Fernando,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 2558 - 2563 (2007/10/03)
Enantioselective copper-catalyzed allylic alkylations were performed on allylic bromides with a protected hydroxyl or amine functional group using several Grignard reagents and Taniaphos L1 as a ligand. The terminal olefin moiety in the products was transformed into various functional groups without racemization, providing facile access to a variety of versatile bifunctional chiral building blocks.
Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones
Myers, Andrew G.,Yang, Bryant H.,Chen, Hou,McKinstry, Lydia,Kopecky, David J.,Gleason, James L.
, p. 6496 - 6511 (2007/10/03)
The use of pseudoephedrine as a practical chiral auxiliary for asymmetric synthesis is described in full. Both enantiomers of pseudoephedrine are inexpensive commodity chemicals and can be N-acylated in high yields to form tertiary amides. In the presence of lithium chloride, the enolates of the corresponding pseudoephedrine amides undergo highly diastereoselective alkylations with a wide range of alkyl halides to afford α-substituted products in high yields. These products can then be transformed in a single operation into highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones.
Highly stereoselective acetylations via norephedrine derived oxazolidines
Bernardi,Cavicchioli,Poli,Scolastico,Sidjimov
, p. 7925 - 7036 (2007/10/02)
Norephedrine derived 2-methoxy-2-methyl oxazolidine 2 is an efficient stereoselective acetylating agent in reactions with stereogenic silylenolethers and silylketenethiolacetals. Moderate selectivity is also obtained upon acetylation of crotyltin reagents
Total Synthesis and Stereochemistry of (+)-Phyllanthocindiol
McGuirk, Paul R.,Collum, David B.
, p. 843 - 852 (2007/10/02)
The total synthesis of (+)-phyllanthocindiol starting with (S)-(+)-3-hydroxy-2-methylpropanoic acid and (S)-(-)-perilla aldehyde is reported.The totally enantioselective sequence elucidated the relative and absolute stereochemistry of (+)-phyllanthocindio
