198561-33-0Relevant academic research and scientific papers
Organocatalysed synthesis of isoxazolines initiated by a chemoselective oxa-Michael reaction of N-BocNHOH
Noel,Gembus,Levacher,Briere
supporting information, p. 1245 - 1249 (2014/03/21)
An organocatalysed and chemoselective one-pot oxa-Michael-cyclocondensation reaction of N-BocNHOH to unsaturated α-ketoesters is reported which affords an original entry to enantioenriched 3-isoxazoline carboxylate derivatives as biorelevant heterocyclic
Total synthesis of a mevinic acid analog
Reddy, Thummalapally Srikanth,Reddy, Dorigondla Kumar,Narasimhulu, Manchala,Ramesh, Dasari,Venkateswarlu, Yenamandra
experimental part, p. 2158 - 2163 (2011/02/17)
Total synthesis of mevinic acid analog 1 has been achieved efficiently starting from chiral 2,3-O-isopropylidene-D-glyceraldehyde (2). The synthesis involves Mitsunobu reaction and Evans' intramolecular oxa-Michael syn-addition reactions as key steps. Cop
Base-catalyzed isomerization of 2-isoxazolines enables a two-step enantioselective synthesis of β-hydroxynitriles from enals
Pohjakallio, Antti,Pihko, Petri M.,Liu, Jun
supporting information; experimental part, p. 6712 - 6715 (2010/12/19)
The asymmetric synthesis of β-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of β-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of β-hydroxynitriles from α,β-unsaturated aldehydes in high enantiomeric purity.
A total synthesis of (+)- and (-)-dihydrokavain with a sonochemical blaise reaction as the key step
Wang, Fang-Dao,Yue, Jian-Min
, p. 2575 - 2579 (2007/10/03)
Starting from 2,3-O-isopropylidene-D-glyceraldehyde (2) as chiral material, the naturally occurring (S)-(+)-dihydrokavain (1a) was synthesized by a procedure that involves a sonochemical Blaise reaction as the key step. The absolute configuration of (S)-(
Method of manufacturing cyano compounds
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Page 9, (2008/06/13)
A method of manufacturing a cyano compound by reacting a carbonyl compound with a nitrile compound having at least one α-hydrogen atom in the presence of a ligand and a metal compound of formula (III), [in-line-formulae]MX??(III) [/in-line-formulae] where
Highly Enantioselective Synthesis of β-Hydroxy Nitriles by the Cyanomethylation of Aldehydes using DPMPM as a Chiral Catalyst or Ligand
Soai, Kenso,Hirose, Yuji,Sakata, Shuichi
, p. 677 - 680 (2007/10/02)
Optically active β-hydroxy nitriles in up to 93percent e.e. were obtained by the enantioselective addition of cyanomethylzinc bromide to aldehydes using DPMPM as a chiral catalyst or ligand.
Enhanced Enantioselectivity of an Enzymatic Reaction by the Sulfur Functional Group. A Simple Preparation of Optically Active β-Hydroxy Nitriles Using a Lipase
Itoh, Toshiyuki,Takagi, Yumiko,Nishiyama, Shigenori
, p. 1521 - 1524 (2007/10/02)
The enantioselectivity of a lipase-catalyzed hydrolysis was improved by varying the acyl residue into the sulfur functional one, i.e. the β-(phenylthio)- or β-(methylthio)acetoxy group, from acetate or valerate to realize satisfactory resolution of β-hydr
Stereorecognition Enhancement by the Sulfur Functional Group in the Lipase Hydrolysis. An Efficient Synthesis of the Optically Active β-Hydroxy Nitriles
Itoh, Toshiyuki,Takagi, Yumiko
, p. 1505 - 1506 (2007/10/02)
β-phenylthio and β-methylthioacetoxy nitriles have been found to be good substrates for the kinetic resolution by lipase to give optically active β-hydroxy nitriles with high enantioselectivity.
