Art

J-GLOBAL ID：201002249505060815   Reference number：10A0232996

CATALYTIC ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF AZOMETHINE IMINES TO ALLYL ALCOHOL UTILIZING TARTARIC ACID ESTER AS A CHIRAL AUXILIARY

キラル補助剤として酒石酸エステルを用いたアゾメチンイミンのアリルアルコールへの触媒不斉1,3-双極環状付加反応

Author (4)： TANAKA Katsuyoshi (Kanazawa Univ., Kanazawa, JPN) ,  KATO Tomomitsu (Kanazawa Univ., Kanazawa, JPN) ,  UKAJI Yutaka (Kanazawa Univ., Kanazawa, JPN) ,  INOMATA Katsuhiko (Kanazawa Univ., Kanazawa, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 80  Issue： 2  Page： 887-893  Publication year： Mar. 01, 2010 
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： reagent ,  *asymmetric synthesis ,  *azomethine ,  *1,3-dipolar cycloaddition ,  stereoselectivity ,  optical activity ,  magnesium bromide ,  catalytic reaction ,  nitrogen heterocyclic compound ,  *dicarboxylic acid ,  *carboxylate (ester) ,  Grignard reagent ,  *imine ,  aliphatic alcohol ,  unsaturated alcohol ,  allyl compound ,  enantiomeric excess ,  enantioselectivity ,  chiral auxiliary ,  *Tartrates
Semi thesaurus term： ピラゾリジン類 ,  *Tartrates

JST classification (3)： Pyrazoles  (CF07082G) ,  Aliphatic alcohols  (CF03090H) ,  Addition reaction,elimination reaction  (CF02030M)

Substance index (4)： Diisopropyl L-tartrate ,  1-Benzylidene-3-oxo-1-pyrazolidinium-2-ide ,  4α-(Hydroxymethyl)-2β-phenyl-1,5-diazabicyclo[3.3.0]octane-6-one ,  Allyl alcohol

Reference (14)：

• A. Padwa,‘Comprehensive Organic Synthesis,’ Vol.4, ed. by B. M. Trost and I. Fleming, Pergamon Press, New York, 1991, pp. 1069-1109.
• K. V. Gothelf,‘Cycloaddition Reactions in Organic Synthesis,’ ed. by S. Kobayashi and K. A. Jørgensen, Wiley-VCH, Weinheim, 2002, Chapter 6; S. Kanemasa,‘Cycloaddition Reactions in Organic Synthesis,’ ed. by S. Kobayashi and K. A. Jørgensen, Wiley-VCH, Weinheim, 2002, Chapter 7; L. M. Stanley and M. P. Sibi, Chem. Rev., 2008, 108, 2887.
• S. Kobayashi, H. Shimizu, Y. Yamashita, H. Ishitani, and J. Kobayashi, J. Am. Chem. Soc., 2002, 124, 13678; R. Shintani and G. C. Fu, J. Am. Chem. Soc., 2003, 125, 10778; Y. Yamashita and S. Kobayashi, J. Am. Chem. Soc., 2004, 126, 11279; S. Shirakawa, P. J. Lombardi, and J. L. Leighton, J. Am. Chem. Soc., 2005, 127, 9974; A. Suárez, C. W. Downey, and G. C. Fu, J. Am. Chem. Soc., 2005, 127, 11244; W. Chen, X.-H. Yuan, R. Li, W. Du, Y. Wu, L.-S. Ding, and Y.-C. Chen, Adv. Synth. Catal., 2006, 348, 1818; H. Suga, A. Funyu, and A. Kakehi, Org. Lett., 2007, 9, 97; W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, and Y.-C. Chen, Angew. Chem. Int. Ed., 2007, 46, 7667; M. P. Sibi, D. Rane, L. M. Stanley, and T. Soeta, Org. Lett., 2008, 10, 2971.
• Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 22, 1847; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 25, 455; Y. Yoshida, Y. Ukaji, S. Fujinami, and K. Inomata, Chem. Lett., 1998, 27, 1023; Y. Ukaji, M. Ima, T. Yamada, and K. Inomata, Heterocycles, 2000, 52, 563; M. Tsuji, Y. Ukaji, and K. Inomata, Chem. Lett., 2002, 31, 1112; Y. Ukaji and K. Inomata, Synlett, 2003, 1075.
• Y. Ukaji, K. Taniguchi, K. Sada, and K. Inomata, Chem. Lett., 1997, 26, 547; D. Xia, K. Taniguchi, Y. Ukaji, and K. Inomata, Chem. Lett., 2001, 30, 468; D. Xia, Y. Ukaji, S. Fujinami, and K. Inomata, Chem. Lett., 2002, 31, 302; D. Xia, K. Taniguchi, Y. Hamamoto, K. Sada, S. Fujinami, Y. Ukaji, and K. Inomata, Bull. Chem. Soc. Jpn., 2006, 79, 1069.

Terms in the title (5)： キラル補助剤 ,  酒石酸エステル ,  アリルアルコール ,  触媒 ,  双極環状付加反応