Ishihara World: Rational Design of High-Performance Catalysts

Based on Acid–Base Combination Chemistry

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▼[Organic Chemistry Portal] C–O Ring Construction:  The Kang/Lee Synthesis of (–)-11β-Hydroxycurvularin

Prof. Douglass F. Taber has cited some of our recent publications in his Highlight column on "C-O Ring Construction" [Organic Chemistry Portal]: The Kang/Lee Synthesis of (-)-11β-Hydroxycurvularin"Kazuaki Ishihara of Nagoya University devised (Chem. Lett. 2016, 45, 353. DOI: 10.1246/cl.160004) the enantioselective oxidative cyclization of 8 to 9."

http://www.organic-chemistry.org/Highlights/2016/14November.shtm

▼Prof. Kazuaki Ishihara received Asian Core Program / Advanced Research Network Lectureship Award (from Coordinator Korea), October 30th, 2016.

PO-C15 "Enantioselective Carbon–Carbon Bond Formation Reactions Induced by Chiral BINSA-Derived Brønsted Acid Catalysts," ACP-2016-Korea (The 11th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-11) & The 2nd Advanced Network on Cutting-Edge Organic Chemistry in Asia (ARNCHOCA-2), Fusion Hall, KI Institute (KAIST), Dajeon, Korea during October 27-30, 2016.

▼IGER Seminar 2016.10.5 (Wed) 16:30-18:00 @ the Venture Hall, 3F, VBL

■Dr. Rong-Jie Chein,
Associate Research Fellow
Institute of Chemistry, Academia Sinica, Taipei, Taiwan R.O.C.
1. Development of ortho-Directed Methodogy
2. Chiral Tetrahydrothiophene Ligands in Asymmetric Catalysis


Regioselective 1,4- and 1,6-Conjugate Additions of Grignard Reagent-Derived Organozinc(II)ates to Polyconjugated Esters
Manabu Hatano, Mai Mizuno, and Kazuaki Ishihara*
Org. Lett. 2016, 18(18), 4462-4465. Org. Lett. 2016, 18(18), 4462-4465.

Publication Date (Web): September 7, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b01774

Regioselective synthetic methods were developed for 1,4- and 1,6-conjugate additions of Grignard reagent-derived organozinc(II)ates to malonate-derived polyconjugated esters. By taking advantage of the tight ion-pair control of organozinc(II)ates, it was possible to switch between 1,4- and 1,6-conjugate additions by introducing a terminal ethoxy moiety in the conjugation.

▼「キラルビナフチルジスルホン酸(BINSA)を用いる精密分子触媒設計」

【特集】ケミカルバイオロジーの新展開

波多野学, 石原一彰, 化学工業 2016, 67(9), 660–667.

http://www.kako-sha.co.jp/newvol.htm#kagaku

アミノ酸をはじめとする天然物や医薬品の多くは光学活性体で,両鏡像体間で生理活性は大きく異なる.従って,有機合成で自由自在に目的の光学活性化合物を得るためには,触媒的不斉合成法の更なる発展が必要である.なかでも,両鏡像体が安価に入手容易な (R)-または(S)-1,1’-ビナフチル-2,2’-ジオール(BINOL)から誘導されるC2対称なキラルビナフチル化合物は,金属イオンに対するキラル配位子やキラル有機分子触媒として優れた機能を発揮し,多くの不斉触媒反応で用いられている1).本稿では,筆者らが取り組んできたキラルビナフチルジスルホン酸(BINSA)を鍵とするキラル酸・塩基複合触媒2,3)による反応開発について紹介する.

Asymmetric Dearomatization Reactions

Chapter 6. Asymmetric Oxidative Dearomatization Reaction
Muhammet Uyanik and Kazuaki Ishihara, pp. 129-151
In "Asymmetric Dearomatization Reactions" edited by Shu-Li You
[ISBN: 978-3-527-33851-1], 424 pages, Wiley-VCH, August 2016.
http://www.wiley.com/WileyCDA/WileyTitle/productCd-3527338519.html

From Biosynthesis to Total Synthesis: Strategies and Tactics for Natural Products
Alexandros L. Zografos
584 pages, Wiley, April 2016, ISBN: 978-1-118-75173-2
Chapter 9: Higher Terpenes and Steroids, pp. 296–330
Kazuaki Ishihara
http://as.wiley.com/WileyCDA/WileyTitle/productCd-1118751736,subjectCd-LS30.html

Enantioselective Bromocyclization of 2-Gernaylphenols Induced by Chiral Phosphite–Urea Bifunctional Catalysts
Yasuhiro Sawamura, Yoshihiro Ogura, Hidefumi Nakatsuji, Akira Sakakura* and Kazuaki Ishihara*
Chem. Commun. 2016, DOI: 10.1039/C6CC00229C
http://pubs.rsc.org/en/content/articlelanding/2016/cc/c6cc00229c#!divAbstract

Chiral phosphite–urea bifunctional catalysts have been developed for the enantioselective bromocyclization of 2-geranylphenols with N-bromophthalimide (NBP) for the first time. The chiral triaryl phosphite moiety activates NBP to generate a bromophosphonium ion. On the other hand, the urea moiety interacts with a hydroxyl group of the substrate through hydrogen bonding interactions. Enantioselectivity is effectively induced through two-point attractive interactions between the catalyst and the substrate.

リン酸の酸・塩基協奏機能を活用したホウ素Lewis酸-キラルリン酸複合高活性触媒の開発

月刊ファインケミカル 2016年2月号 pp. 24–32.

【特集】不斉合成の進展と最新研究(2016年2月15日発行)
波多野学、石原一彰
http://www.cmcbooks.co.jp/products/detail.php?product_id=5060

Recruit

ポスドク及び大学院生を募集中です。

当研究室では学部生、大学院生の研究室見学を随時受け付けております。

希望者は、石原教授までメールでお問い合わせ下さい。

 

Postdoctoral and graduate students is being recruited.In our laboratory will be accepted at any time undergraduate, graduate student visits to laboratories.Those who wish, please contact us by e-mail to Professor Ishihara.

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ISHIHARA GROUP

名古屋大学

大学院工学研究科 有機・高分子化学専攻(工学部 化学生命工学科)
有機化学講座

触媒有機合成学研究グループ

〒464-8603 名古屋市千種区不老町

B2-3(611)

 

Laboratory of Catalysis in Organic Synthesis, Research Group of Molecular Chemistry, Graduate Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering (Undergraduate Department of Chemistry and Biotechnology, School of Engineering), Nagoya University

B2-3(611), Furo-cho, Chikusa, Nagoya 464-8603, Japan