- Diastereoselective conjugate 1,6-addition of lithium amides to naphthyloxazolines. Mechanistic studies and synthesis of δ-amino acid derivatives
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The novel 1,6-amino addition reaction to the naphthalene ring system followed by the electrophilic alkylation is presented. The detailed mechanistic studies suggest the existence of two equilibrations that result in the 1,4-amino addition reaction and the 1,6-amino addition reaction. The stability and bulkiness of lithium amide play a key role in directing the course of the reaction. The transformation of the 1,6-amino adducts to other useful compounds is concisely demonstrated. The methodology provides a remote-controlled diastereoselective synthesis of δ-amino acid derivatives.
- Shimano, Masanao,Matsuo, Atsushi
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- Oxazolinyl-Assisted Ru(II)-Catalyzed C-H Allylation with Allyl Alcohols and Synthesis of 4-Methyleneisochroman-1-ones
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We report herein a ruthenium-catalyzed, oxazoline-directed strategy for C-H allylation of aryl oxazolines using allylic alcohols as the coupling partner. The present transformation unravels the unusual reactivity of allylic alcohols in the synthesis of 4-
- Singh, Diksha,Kumar, Gangam Srikanth,Kapur, Manmohan
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p. 12881 - 12892
(2019/09/30)
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- Oxazolinyl-Assisted Ru(II)-Catalyzed C?H Functionalization Based on Carbene Migratory Insertion: A One-Pot Three-Component Cascade Cyclization
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A rare, ruthenium-catalyzed, oxazolinlyl assisted C?H functionalization and three-component cascade cyclization for the synthesis of isoquinolinones via a metal-carbene migratory insertion is reported. The transformation is unique since it involves the fo
- Kumar, Gangam Srikanth,Khot, Nandkishor Prakash,Kapur, Manmohan
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supporting information
p. 73 - 78
(2018/12/11)
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- A 2 - aryl - 2 - oxazoline preparation method
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The invention discloses a 2-aryl-2-oxazoline preparation method and belongs to the field of chemistry. According to the method, an aryl-amide compound and 1,2-dichloroethane are reacted for synthesis, and the synthesis reaction is conducted under the alka
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Paragraph 0007; 0015; 0016
(2017/06/21)
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- A general and efficient palladium-catalyzed carbonylative synthesis of 2-aryloxazolines and 2-aryloxazines from aryl bromides
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Oxazoline is OK! A general and efficient method for the synthesis of oxazolines has been developed (see scheme). This allowed the preparation of 27 five-membered-ring heterocycles and 11 six-membered-ring heterocycles in moderate to good yields. Copyright
- Wu, Xiao-Feng,Neumann, Helfried,Neumann, Stephan,Beller, Matthias
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p. 13619 - 13623
(2013/01/15)
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- An efficient oxidative conversion of aldehydes into 2-substituted 2-oxazolines using 1,3-diiodo-5,5-dimethylhydantoin
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Various aromatic and aliphatic aldehydes were converted into the corresponding 2-aryl and 2-alkyl-2-oxazolines, respectively, in good to high yields by reaction with 2-aminoethanol and 1,3-diiodo-5,5-dimethylhydantoin. Moreover, chiral bis-2-oxazolines, which can be used as chiral ligands in asymmetric synthesis, could be also prepared in moderate yields by the reaction of dialdehydes with (R)-(-)-2-phenylglycinol under the same conditions. Georg Thieme Verlag Stuttgart.
- Takahashi, Shogo,Togo, Hideo
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experimental part
p. 2329 - 2332
(2010/03/01)
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- Practical reduction of oxazolines to alcohols
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A two-step, one-pot procedure using methyl chloroformate and lithium borohydride was developed to transform 2-substituted-oxazolines into alcohols. This methodology is compatible with a wide range of substrates including heterocyclic, aromatic, and aliphatic functionalized 2-oxazolines. Best results are obtained with electron-rich and ortho substituted 2-aryl-oxazolines.
- Bernardi, Anna,Ouellet, Stéphane G.,Angelaud, Remy,O'Shea, Paul D.
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supporting information; experimental part
p. 6707 - 6708
(2009/04/07)
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- Direct oxidative conversion of aldehydes and alcohols to 2-imidazolines and 2-oxazolines using molecular iodine
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Aldehydes were converted to the corresponding 2-imidazolines and 2-oxazolines in good yields by the reaction with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate. Moreover, primary alcohols were directly converted to the corresponding 2-imidazolines and 2-oxazolines via aldehydes in one-pot manner with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate.
- Ishihara, Midori,Togo, Hideo
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p. 1474 - 1480
(2007/10/03)
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- A convenient synthesis of oxazolines and imidazolines from aromatic aldehydes with pyridinium hydrobromide perbromide in water
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Various 2-oxazolines were prepared from aromatic aldehydes and 2-aminoethanol with pyridinium hydrobromide perbromide in water at room temperature. 2-Imidazolines were also obtained in good yields from aromatic aldehydes and ethylenediamine under the same reaction conditions. Georg Thieme Verlag Stuttgart.
- Sayama, Shinsei
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p. 1479 - 1484
(2007/10/03)
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