Art

J-GLOBAL ID：201702231332149456   Reference number：17A0599942

GOLD(III)-CATALYZED SYNTHESIS OF 2,3,4-TRISUBSTITUTED DIHYDROPYRANS FROM PROPARGYLIC ALCOHOLS WITH 1,3-DICARBONYL COMPOUNDS

1,3-ジカルボニル化合物によるプロパルギルアルコール類からの2,3,4-三置換ジヒドロピランの金(III)接触合成

Author (7)： MORITA Nobuyoshi (Showa Pharmaceutical Univ., Tokyo, JPN) ,  OGURO Kazuki (Showa Pharmaceutical Univ., Tokyo, JPN) ,  TAKAHASHI Saori (Showa Pharmaceutical Univ., Tokyo, JPN) ,  KAWAHARA Midori (Showa Pharmaceutical Univ., Tokyo, JPN) ,  BAN Shintaro (Showa Pharmaceutical Univ., Tokyo, JPN) ,  HASHIMOTO Yoshimitsu (Showa Pharmaceutical Univ., Tokyo, JPN) ,  TAMURA Osamu (Showa Pharmaceutical Univ., Tokyo, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 95  Issue： 1  Page： 172-180  Publication year： Jan. 25, 2017 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： chemical synthesis ,  catalytic reaction ,  transition metal catalyst ,  gold complex ,  silver catalyst ,  silver compound ,  substitution reaction ,  *cyclization reaction ,  *oxygen heterocyclic compound ,  carboxylate(ester) ,  *carbonyl compound ,  acetylenic compound ,  diol ,  reaction mechanism ,  aliphatic ketone ,  diketone ,  aliphatic carboxylic acid ,  keto acid
Semi thesaurus term： dicarbonyl compound ,  dihydropyran derivative ,  Au catalyst

JST classification (2)： Pyranes  (CF07092R) ,  Catalytic reactions in general  (CB06080F)

Substance index (12)： Acetylacetone ,  2-Phenyl-5,6,9,10-tetrahydro-2,6-methano-4H-1,3-benzodioxocin-7(8H)-one ,  2-Methyl-4-(2-oxooctyl)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester ,  2-Methyl-4-(2-oxo-2-cyclohexylethyl)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester ,  2-Methyl-4-(2-oxo-3,3-dimethylbutyl)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester ,  2-Methyl-4-phenacyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester ,  Acetoacetic acid methyl ,  3-Hydroxy-2-cyclohexen-1-one ,  4-Undecyne-1,3-diol ,  5-Phenyl-4-pentyne-1,3-diol ,  α-(2-Methyl-3-acetyl-5,6-dihydro-4H-pyran-4-yl)acetophenone ,  3-Oxo-3-phenylpropanoic acid ethyl

Reference (12)：

• For synthesis of natural dihydropyrans and tetrahydropyrans, see: (a) T. Martín, J. I. Padrón, and V. S. Martín, Synlett, 2014, 25, 12; (b) N. M. Nasir, K. Ermanis, and P. A. Clarke, Org. Biomol. Chem., 2014, 12, 3323; (c) C. Olier, M. Kaafarani, S. Gastaldi, and M. P. Bertrand, Tetrahedron, 2010, 66, 413; (d) A. B. Smith III, R. J. Fox, and T. M. Razler, Acc. Chem. Res., 2008, 41, 675; (e) K.-S. Yeung, and I. Paterson, Chem. Rev., 2005, 105, 4237; (f) I. Kadota and Y. Yamamoto, Acc. Chem. Res., 2005, 38, 423; (g) T. Yasumoto and M. Murata, Chem. Rev., 1993, 93, 1897.
• N. Morita, A. Yasuda, M. Shibata, S. Ban, Y. Hashimoto, I. Okamoto, and O. Tamura, Org. Lett., 2015, 17, 2688.
• N. Morita, T. Tsunokake, Y. Narikiyo, M. Harada, T. Tachibana, Y. Saito, S. Ban, Y. Hashimoto, I. Okamoto, and O. Tamura, Tetrahedron Lett., 2015, 56, 6269.
• N. Morita, Y. Saito, A. Muraji, S. Ban, Y. Hashimoto, I. Okamoto, and O. Tamura, Synlett, 2016, 27, 1936.
• N. Morita, M. Miyamoto, A. Yoda, M. Yamamoto, S. Ban, Y. Hashimoto, and O. Tamura, Tetrahedron Lett., 2016, 47, 4460.

Terms in the title (5)： ジカルボニル化合物 ,  プロパルギルアルコール類 ,  置換 ,  ジヒドロピラン ,  金