Application of Rh-Catalyzed Cyclization to the Formation of a Chiral Quaternary Carbon

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概要

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• Rh-Catalyzed cyclization was applied to the formation of a chiral quaternary carbon. It has become clear that the Rh-complex can discriminate between isopropenyl and 2-isopentenyl (or isopentyl) substituents, and the cyclization afforded 3,3,4-trisubstituted cyclopentanones with a chiral quaternary carbon in a stereoselective manner. The cyclization of 4-pentenals 6a, b by an achiral neutral Rh(PPh_3)_3Cl afforded 3,3,4-cis-trisubstituted cyclopentanones (±)-7a, b in 86-96%, and the cyclization by a cationic Rh[(R)-BINAP]ClO_4 afforded 3,3,4-trans-trisubstituted cyclopentanones (-)-8a, b of 82-86% ee in 88-98% yields. The mechanism of stereoselection by Rh-complexes is also discussed.

• 社団法人日本薬学会の論文
• 2000-11-01

著者

• 田中 正一

  Graduate School Of Pharmaceutical Sciences Kyushu University

• Imai Masanori

  Graduate School Of Pharmaceutical Sciences Kyushu University

• TANAKA Masakazu

  Graduate School of Pharmaceutical Sciences, Kyushu University

• SUEMUNE Hiroshi

  Graduate School of Pharmaceutical Sciences, Kyushu University

• Sakai K

  Graduate School Of Pharmaceutical Sciences Kyushu University

• Tanaka M

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• Imai Masanori

  Graduate School Of Bioagricultural Sciences Nagoya University

• TAKAHASHI Miyuki

  Graduate School of Pharmaceutical Sciences, Kyushu University

• SAKAMOTO Eishi

  Graduate School of Pharmaceutical Sciences, Kyushu University

• FUNAKOSHI Kazuhisa

  Graduate School of Pharmaceutical Sciences, Kyushu University

• SAKAI Kiyoshi

  Graduate School of Pharmaceutical Sciences, Kyushu University

• Takahashi Miyuki

  Graduate School Of Pharmaceutical Sciences Kyushu University

• Sakai K

  Tohoku Pharmaceutical Univ. Miyagi Jpn

• Sakai K

  Yaizu Suisan Kagaku Industry Co.

• Sakamoto Eishi

  Graduate School Of Pharmaceutical Sciences Kyushu University

• Suemune H

  Graduate School Of Pharmaceutical Sciences Kyushu University

• Suemune Hiroshi

  Graduate School Of Pharmaceutical Sciences Kyushu University

• Tanaka Masakazu

  Graduate School Of Comprehensive Human Sciences University Of Tsukuba

• Funakoshi K

  Graduate School Of Pharmaceutical Sciences Kyushu University

• Imai Miwa

  Department of Biochemistry, Kyoritsu University of Pharmacy

• TANAKA Masakazu

  Graduate School of Agriculture, Hokkaido University

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