Stereoselective synthesis of alkenes using new Julia-type reagents

• Project/Area Number: 25410111
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Gifu University
• Principal Investigator: Ando Kaori 岐阜大学, 工学部, 教授 (70211018)
• Co-Investigator(Renkei-kenkyūsha): OKA NATSUHISA 岐阜大学, 工学部, 准教授 (50401229)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000); Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: シス‐オレフィン / Julia-Kocienski reaction / アルケン合成 / 立体選択的 / Julia形オレフィン化反応 / スルホンアニオン / メチレン化剤 / シス-1,3-ジエン / オレフィン化反応 / カルボニル化合物 / 立体選択性 / Julia型反応 / テトラゾイルスルホン / Julia-Kocienski反応 / 合成化学

Outline of Final Research Achievements

Although Julia-Kocienski reaction is a efficient tool for direct trans-alkene synthesis via metalated tetrazolylsulfones with aldehydes, cis-selective reagents are also needed. In this study, we developed a practical methylenation reation for aldehydes and ketones using new Julia-type reagents. Based on this results, we also found cis selective reaction for the synthesis of 1,3-dienes.

Research Products

• [Journal Article] Sodium Amide Induced Cyclization of 2-Iodoprop-2-enylamines: Application to the Synthesis of 1-Aryl-2-methyleneaziridines (2015)
  • Author(s): Bayliffe, F. H.; Steven, A.; Ando, K.; Shipman, M.
  • Journal Title: Synlett Volume: 26 Issue: 10 Pages: 1371-1374
  • DOI: 10.1055/s-0034-1380521
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Practical methylenation reaction for aldehydes and ketones using new Julia-type reagents (2015)
  • Author(s): Ando, K.; Kobayashi T.; Uchida, N.
  • Journal Title: Organic Letters Volume: 17 Issue: 10 Pages: 2554-2557
  • DOI: 10.1021/acs.orglett.5b01049
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Stereoselective Synthesis of Z-a,b-Unsaturated Sulfones Using New Peterson Reagents (2015)
  • Author(s): Ando, K., Wada, T.; Okumura, M.; Sumida, H.
  • Journal Title: Organic Letters Volume: 17 Issue: 24 Pages: 6026-6029
  • DOI: 10.1021/acs.orglett.5b03008
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Sodium Amide Induced Cyclization of 2-Iodoprop-2-enylamines: Application to the Synthesis of 1-Aryl-2-methyleneaziridine (2015)
  • Author(s): Bayliffe, F. H.; Steven, A.; Ando, K.; Shipman, M.
  • Journal Title: Synlett Volume: 2015
  • Peer Reviewed
• [Journal Article] -Selective Ribofuranosylation of Alcohols with Ribofuranosyl Iodides and Triphenylphosphine Oxide (2014)
  • Author(s): Oka, N.; Kajino, R.; Takeuchi, K.; Nagakawa, H.; Ando, K.
  • Journal Title: J. Org. Chem. Volume: 79 Issue: 16 Pages: 7656-7664
  • DOI: 10.1021/jo500632h
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] 理論計算の有機合成への活用 (2014)
  • Author(s): 安藤香織
  • Journal Title: 有機合成化学協会誌 Volume: 72 Pages: 890-898
  • NAID: 130004691489
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Highly Z-Selective Synthesis of a,b-Unsaturated Nitriles Using Horner-Wadsworth-Emmons Reaction. (2013)
  • Author(s): Kaori Ando, Miho Okumura, Shigeo Nagaya
  • Journal Title: Tetrahedron Lett. Volume: 54 Issue: 15 Pages: 2026-2028
  • DOI: 10.1016/j.tetlet.2013.02.020
  • Peer Reviewed
• [Journal Article] 35. Synthesis of inosine 6-phosphate diesters via phosphitylation of the carbonyl oxygen (2013)
  • Author(s): Oka, N.; Morita, Y.; Itakura, Y.; Ando, K.
  • Journal Title: Chem. Commun. Volume: 49 Issue: 98 Pages: 11503-11505
  • DOI: 10.1039/c3cc46617e
  • Peer Reviewed
• [Journal Article] Purification and comparison of native and recombinant tRNA-guanine transglycosylases from Methanosarcina acetivorans. (2013)
  • Author(s): Nomura, Y, Onda, Y, Ohno, S, Taniguchi, H, Ando, K, Oka, N, Nishikawa, K, Yokogawa, T
  • Journal Title: Protein Expr. Purif. Volume: 88 Issue: 1 Pages: 13-19
  • DOI: 10.1016/j.pep.2012.11.009
  • Peer Reviewed
• [Presentation] アルケンの立体化学を制御する－PとSとSiの化学 (2016)
  • Author(s): 安藤香織
  • Organizer: 有機合成2月セミナー「有機合成のニュートレンド2016」
  • Place of Presentation: 大阪
  • Year and Date: 2016-02-03
  • Invited
• [Presentation] Highly practical new methylenation reagent for aldehydes and ketones (2015)
  • Author(s): Kaori Ando, Takahisa Kobayashi, Nariaki Uchida
  • Organizer: The 2015 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] 新Julia型オレフィン化試薬を用いるメチレン化とcis-1,3-ジエンの合成 (2015)
  • Author(s): 小林峻久、内田成晃、安藤香織
  • Organizer: 第４２回有機典型元素化学討論会
  • Place of Presentation: 名古屋
  • Year and Date: 2015-12-03
• [Presentation] Highly Practical New Methylenation Reagent for Aldehyde and Ketones (2015)
  • Author(s): 安藤香織
  • Organizer: 日本プロセス化学会2015ウィンターシンポジウム
  • Place of Presentation: 徳島
  • Year and Date: 2015-11-27
  • Invited
• [Presentation] Highly practical new methylenation reagent for aldehydes and ketones (2015)
  • Author(s): Kaori Ando, Takahisa Kobayashi, Nariaki Uchida
  • Organizer: The 3rd International Symposium on Process Chemistry
  • Place of Presentation: 京都
  • Year and Date: 2015-07-14
  • Int'l Joint Research
• [Presentation] 新しいJulia型メチレン化試薬の開発 (2015)
  • Author(s): 小林峻久、内田成晃、安藤香織
  • Organizer: 日本化学会第95回春季年会
  • Place of Presentation: 船橋
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] 新Julia-Kocienski型試薬を用いる高Ｚ選択的1,3-ジエンの合成 (2015)
  • Author(s): 浅野秀紀、河野大喜、瀬見井優、安藤香織
  • Organizer: 日本化学会第95回春季年会
  • Place of Presentation: 船橋
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] Julia-Kocienski試薬の置換基効果の研究と新オレフィン化試薬の開発 (2014)
  • Author(s): 浅野秀紀、河野大喜、瀬見井優、安藤香織
  • Organizer: 第45回中部化学関係学協会支部連合秋季大会
  • Place of Presentation: 中部大学、名古屋
  • Year and Date: 2014-11-29 – 2014-11-30
• [Presentation] 新しいJulia-Kocienskiオレフィン化試薬の開発 (2014)
  • Author(s): 鷲見俊秀、河野大喜、瀬見井優、安藤香織
  • Organizer: 第３４回有機合成若手セミナー
  • Place of Presentation: 大阪大学豊中キャンパス
  • Year and Date: 2014-08-05
• [Presentation] 新しいJulia型メチレン化試薬の開発 (2014)
  • Author(s): 小林峻久、内田成晃、安藤香織
  • Organizer: 第３４回有機合成若手セミナー
  • Place of Presentation: 大阪大学豊中キャンパス
  • Year and Date: 2014-08-05
• [Presentation] One-pot preparation of Z-a,b-unsaturated esters by oxidation of alcohols and the Horner-Wadsworth-Emmons reaction (2013)
  • Author(s): Chika Takaba, Kaori Ando
  • Organizer: Nagoya Symposium 2013, Nagoya
  • Place of Presentation: 名古屋大学
• [Presentation] Highly E-selective Solvent-Free Horner-Wadsworth-Emmons Reactioｎ (2013)
  • Author(s): Nariaki Uchida, Kyohei Yamada, Kaori Ando
  • Organizer: Nagoya Symposium 2013, Nagoya
  • Place of Presentation: 名古屋大学
• [Presentation] The synthetic mechanism of tRNA modificarions in thermophilic bacteria (2013)
  • Author(s): Takuya Kawamura, Chie Tomikawa, Tahayuki Ohira, Yasushi Inoue, Nobukazu Nameki, Natsuhisa Oka, Hiroki Taniguchi, Kaori Ando, Satoshi Ohno, Akihiko Yamagishi, Tsutom Suzuki, Takashi Yokogawa, Hiroyuki Hori
  • Organizer: Riboclub 2013 Annual Meeting, Canada
  • Place of Presentation: Canada
• [Presentation] 新しいJulia-Kocienskiオレフィン化試薬の開発 (2013)
  • Author(s): 鷲見俊秀、河野大喜、瀬見井優、安藤香織
  • Organizer: 第４３回複素環化学討論会、岐阜
  • Place of Presentation: 岐阜国際会議場
• [Presentation] ヨウ化糖を用いるアルコールのα選択的リボフラノシル化反応の開発 (2013)
  • Author(s): 梶野 麟、岡 夏央、竹内 薫、永川晴奈、安藤香織
  • Organizer: 第４３回複素環化学討論会、岐阜
  • Place of Presentation: 岐阜国際会議場
• [Presentation] ピーターソン・オレフィン化反応によるZ-a,b-不飽和スルホンの立体選択的合成 (2013)
  • Author(s): 住田 大、奥村美穂、安藤香織
  • Organizer: 第４０回有機典型元素化学討論会、東大阪
  • Place of Presentation: 近畿大学
• [Presentation] Julia-Kocienski試薬の置換基効果の研究と新しいオレフィン化試薬の開発 (2013)
  • Author(s): 浅野秀紀、河野大喜、瀬見井優、安藤香織
  • Organizer: 第４０回有機典型元素化学討論会、東大阪
  • Place of Presentation: 近畿大学
• [Remarks] 岐阜大学 工学部 化学・生命工学科 安藤研究室
  • URL: http://www1.gifu-u.ac.jp/~ando_ap/