Major research fields
Synthetic Organic Chemistry, Process Chemistry
Organic syntheses from a viewpoint point of the green chemistry have nowadays important positions in environmentally benign chemical productions. Our research in directed at this aim and focuses on the development of new, original, useful, and practical organic reactions from the recent green chemical standpoint, especially for the process chemistry. Their applications to short-step syntheses of fine chemicals such as pharmaceuticals, agrochemicals, and biologically active natural products are also included. The studies involve six main subjects listed as follows: (1) Exploitation of Crossed Ti-Zr-Claisen condensations, the related Ti-direct aldol additions, Mannich reactions, and Michael additions, and application of these Ti-and Zr-mediated reactions for the production of useful fine chemicals such as musk perfume (Z)-civetone, R-muscone, R-mintlactone, R-menthofuran, cis-jasmone (its lactone analog), and 1β-methylcarabapenems. (2) Development of totally cost-effective, mild, and robust condensation reactions and esterifications and amide formations of carboxylic acids (or acid chlorides) with alcohols and amines, respectively. (3) Development of mild but powerful sulfonylations and silylations of a wide variety of alcohols. (4) Exploitation of practically useful (E)- and (Z)-stereocomplementally preparations of a,b-unsaturated esters utilizing sequential stereoselective enol tosylations and stereoretentive cross-coupling reactions. (5) Exploitation of useful organic syntheses based on characteristic properties cyclopropanes such as the regiocontrolled benzannulation and the chirality exchange from sp3 central chirality into axial chirality and its application to total synthesis of natural lignan lactone natural products. (6) Synthetic studies on the stereostructure-activity relationship of biologically active pharmaceuticals, perfumes, and agrochemicals.
Major relevant publications
- Yoshinori Nishii, Kazunori Wakasugi, Kenji Koga, Yoo Tanabe, “Chirality Exchange from sp³ Central Chirality to Axial Chirality: Benzannulation of Optically Active Diaryl-2,2-dichrolocyclopropylmethanols to Axially Chiral a-Arylnaphthalenes,” J. Am. Chem. Soc. 2004, 126, 5358-5359.
- Tomonori Misaki, Rhohei Nagase, Kunshi Matsumoto, Yoo Tanabe, “Ti-Crossed Claisen Condensation between Carboxylic Esters and Acid Chlorides or Acids: Highly Selective and General Method for the Preparation of Various b-Keto Esters,” J. Am. Chem. Soc. 2005, 127, 2854-2855.
- Takeshi Funatomi, Kazunori Wakasugi, Tomonori Misaki, Yoo Tanabe, “Pentafluorophenylammonium triflate (PFPAT): Efficient, practical, and cost-effective catalyst for esterification, thioesterification, transesterification, and macrolactone formation,” Green Chem. 2006, 8, 1022-1027. Frontcover Article.
- Ryohei Nagase, Yumiko Oguni, Satoko Ureshino, Hiroaki Mura, Tomonori Misaki, Yoo Tanabe, “Asymmetric Ti-Crossed Claisen Condensation: Application to Concise Asymmetric Total Synthesis of Alternaric Acid,” Chem. Commun. 2013, 49, 7001-7003.
- Yuichiro Ashida, Yuka Sato, Takeyuki Suzuki, Kanako Ueno, Ken-ichiro Kai, Hidefumi, Nakatsuji, Yoo Tanabe, “(E)-, (Z)-Parallel Preparative Methods for Stereodefined b,b-Diaryl- and a,b-Diaryl-a,b-unsaturated Esters: Application to Stereocomplementary Concise Synthesis of Zimelidine,” Chem. Eur. J. 2015, 21, 5934-5945.