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翻訳と辞書　辞書検索 [ 開発暫定版 ] スポンサード リンク Asymmetric Keck allylation ： ウィキペディア英語版 Asymmetric Keck allylation The asymmetric Keck allylation is a chemical reaction that involves the addition of allyl group to an aldehyde. ==Background== Laszlo Kuerti and Barbara Czako provide a superb review of many reactions in organic chemistry, including the Keck allylation; their text describes the importance of this reaction, the themes of which have been ordered similarly here.〔Kuerti, L., Czako, B., Strategic Applications of Named Reactions in Organic Synthesis. London, UK: Elsevier, 2005. Print.〕 Secondary homoallylic alcohols are important moieties in organic synthesis, used in intermediates in the production of (−)-Gloeosporone,〔Fuerstner, A., Langemann, K., J. Am. Chem. Soc. 1997, 119, 9130-9136.〕 Epothilone A,〔Meng, D., Bertinato, P., Balog, A., Su, D. –S., Kamanecka, T., Sorensen, E., Danishefsky, S. J., J. Am. Chem. Soc. 1997, 119, 10073-10092〕 the CD-Subunit of spongistatins,〔Smith, A. B., III, Doughty, V. A., Sfouggatakis, C., Bennett, C. S., Koyanagi, J., Takeuchi, M., Org. Lett., 2002, 4, 783-786.〕 and the C10-C20 Subunit of rhizoxin A,〔Keck, G. E., Wager, C. A., Wager, T. T., Savin, K. A., Covel, J. A., McLaws, M. D., Krishnamurthy, D., Cee, V. J., ACIEE 2001, 40, 231-234.〕 among other natural products. The Keck allylation has also been utilized to form substituted tetrahydropyrans enantioselectively, moieties found in products such as phorboxazole and bryostatin 1.〔Keck, G. E., Covel, J. A., Schiff, T., Yu, T., Org. Lett., 2002, 4, 1189-1192.〕 The general reaction scheme follows: Although the groups of E. Tagliavini and K. Mikami reported the catalysis of this reaction using a Ti(IV) BINOL complex in the same year,〔Aoki, S., Mikami, K., Terada, M., Nakai, T., Tetrahedron 1993, 49, 1783-1792.〕〔Costa, A. L., Piazza, M. G., Tagliavini, E., Trombini, C., Umani-Ronchi, A., J. Am. Chem. Soc., 1993, 115, 7001-7002.〕Keck’s seminal publication reported asymmetric allylation with higher enantio- and diastereoselectivity using Ti(IV)-BINOL prepared by mixing Ti(Oi-Pr)4 in dichloromethane at room temperature for between 5 minutes and 1 hour, without the use of 4 Angstrom molecular sieves as in Mikami’s procedure, or excess of BINOL as in Tagliavini’s procedure.〔Keck, G. E., Geraci, L. S., Tetrahedron Lett. 1993, 34, 7827-7828.〕 Keck’s early success with stereoselectivity and the simplicity of the catalyst preparation led to many improvements in reaction design, including development of BINOL derivatives, addition of stoichiometric additives to enhance rate, and extension of scope to substituted stannane nucleophiles. 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Asymmetric Keck allylation」の詳細全文を読む スポンサード リンク 翻訳と辞書 : 翻訳のためのインターネットリソース Copyright(C) kotoba.ne.jp 1997-2016. All Rights Reserved.