67928-91-0Relevant academic research and scientific papers
Enantioselective synthesis of isotopically labeled homocitric acid lactone
Moore, Jared T.,Hanhan, Nadine V.,Mahoney, Maximillian E.,Cramer, Stephen P.,Shaw, Jared T.
, p. 5615 - 5617 (2013)
A concise synthesis of homocitric acid lactone was developed to accommodate systematic placement of carbon isotopes (specifically 13C) for detailed studies of this cofactor. This new route uses a chiral allylic alcohol, available in multigram quantities from enzymatic resolution, as a starting material, which transposes asymmetry through an Ireland-Claisen rearrangement.
Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkoxy Esters
Podunavac, Ma?a,Lacharity, Jacob J.,Jones, Kerry E.,Zakarian, Armen
supporting information, p. 4867 - 4870 (2018/08/24)
A systematic investigation into the Ireland-Claisen rearrangement of α-alkoxy esters is reported. In all cases, the use of KN(SiMe3)2 in toluene gave rearrangement products corresponding to a Z-enolate intermediate with excellent diastereoselectivity, presumably because of chelation control. On the other hand, chelation-controlled enolate formation could be overcome for most substrates through the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).
Total synthesis of umuravumbolide and hyptolide through silicon-tethered ring-closing metathesis
Chowdhury, Partha Sarathi,Kumar, Pradeep
, p. 4586 - 4593 (2013/07/26)
The total synthesis of umuravumbolide and hyptolide has been achieved in a efficient manner by using temporary silicon-tethered ring-closing metathesis and cross-coupling reactions as key steps. The stereogenic centres were generated by means of proline-catalysed α-aminoxylation of aldehydes and Brown's asymmetric allylation method. An efficient total synthesis of umuravumbolide and hyptolide has been achieved by using temporary silicon-tethered ring-closing metathesis. The stereogenic centres were generated by using asymmetric allyl boration and proline-catalysed α-aminoxylation with high degrees of enantioselectivity. Copyright
Stereoselective synthesis of umuravumbolide
Kumar, T. Vijaya,Reddy, G. Venkateswar,Babu, K. Suresh,Rao, J. Madhusudana
, p. 594 - 598 (2013/06/27)
An efficient stereoselective total synthesis of umuravumbolide has been developed. The key features of the synthesis include Jacobsen resolution, Wadsworth Emmons olefination and silyl-tethered ring closing metathesis.
Catalytic enantioselective addition of alkyl grignard reagents to aliphatic aldehydes
Fernandez-Mateos, Emilio,Macia, Beatriz,Yus, Miguel
supporting information, p. 1249 - 1254 (2013/06/27)
Herein, we report an efficient catalytic system for the enantioselective addition of alkyl Grignard reagents to a broad range of aliphatic aldehydes with good yields and enantioselectivities. Remarkably, the challenging methylmagnesium bromide (MeMgBr) can also be added to a variety of aliphatic aldehydes, providing versatile chiral methyl carbinol units with unprecedented yields and enantioselectivities in a simple one-pot procedure under mild conditions. Copyright
Stereoselective synthesis of pectinolide C
Kumar, T. Vijaya,Shankaraiah,Babu, K. Suresh,Rao, J. Madhusudana
, p. 1397 - 1400 (2013/04/10)
The first total synthesis of the pectinolide C has been accomplished using the silyl-tethered ring closing metathesis, Jacobsen resolution, and Wadsworth-Emmons olefinations as key reaction sequences. Copyright
The substrate spectrum of the inverting sec-alkylsulfatase Pisa1
Schober, Markus,Knaus, Tanja,Toesch, Michael,MacHeroux, Peter,Wagner, Ulrike,Faber, Kurt
, p. 1737 - 1742 (2012/07/31)
The substrate spectrum of the inverting alkylsulfatase Pisa1 was investigated using a range of sec-alkyl sulfate esters bearing aromatic, olefinic and acetylenic moieties. Perfect enantioselectivities were obtained for substrates bearing groups of different size adjacent to the sulfate ester moiety. Insufficient selectivities could be doubled by using dimethyl sulfoxide (DMSO) as co-solvent. Hydrolytically unstable benzylic sulfate esters could be sufficiently stabilised by introduction of electron-withdrawing substituents. Overall, Pisa1 appears to be a very useful inverting alkylsulfatase for the deracemisation of rac-sec-alcohols via enzymatic hydrolysis of their corresponding sulfate esters, which furnishes homochiral products possessing the 'anti-Kazlauskas' configuration. Copyright
Catalytic ring expansion of vinyl oxetanes: Asymmetric synthesis of dihydropyrans using chiral counterion catalysis
Guo, Boying,Schwarzwalder, Gregg,Njardarson, Jon T.
, p. 5675 - 5678 (2012/07/03)
Acid Showdown! The first catalytic ring expansion of vinyl oxetanes to 3,6-dihydro-2H-pyrans is described. Copper(II) triflate emerged as the best catalyst for this new transformation, which has broad scope as demonstrated by the eighteen examples included. The symmetric vinyl oxetane substrate can be asymmetrically desymmetrized when using either chiral Lewis or Bronsted acids as catalysts. Copyright
First example of hydrolytic kinetic resolution of acrylate of secondary alcohols by lipase Amano AK
Bora, Pranjal P.,Bez, Ghanashyam,Anal, Jasha Momo H.
experimental part, p. 270 - 275 (2012/07/03)
Lipase Amano AK is found to be extremely efficient catalyst for hydrolytic kinetic resolution of acrylates of secondary alcohols in aqueous phosphate buffer at pH 7.0. Both aliphatic and benzylic secondary alcohols show good to excellent E values.
Syntheses of aggregation pheromones of the palm weevils rhyncophorus vulneratus and rphoenicis and of (+)- trans-whiskey lactone
Yadav,Rao, C. Venkateshwar,Prasad,Khazim Al Ghamdi, Ahmad Al
, p. 3894 - 3898 (2012/01/06)
(3S,4S)-3-Methyloctan-4-ol, (4S,5S)-4-methylnonan-5-ol, and (+)-trans-whiskey lactone [(4S,5R)-5-butyl-4-methyldihydrofuran-2(3H)-one] were synthesized stereoselectively by using a radical cyclization reaction as a key step. All three molecules were synthesized from a common cyclic acetal intermediate. Georg Thieme Verlag Stuttgart. New York.
