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3 results on '"Toshiaki Tatematsu"'

1. New Methods and Reagents in Organic Synthesis 89. Studies on Reaction Conditions and New Entry to Chiral Ligands in the Chiral Lithium Amide-Mediated Enantioselective Aldol Reaction

Author

Takayuki Shioiri, Toshiaki Tatematsu, and A. Ando

Subjects
Chiral auxiliary, Lithium amide, Enantioselective synthesis, Ether, General Chemistry, General Medicine, Medicinal chemistry, Lithium diisopropylamide, chemistry.chemical_compound, chemistry, Aldol reaction, Drug Discovery, Stereoselectivity, Enantiomeric excess
Abstract

Reaction conditions for the enantioselective aldol reaction of 2, 2-dimethyl-3-pentanone (3) and benzaldehyde using the chiral lithium amide 1b as a chiral auxiliary were thoroughly investigated. All three procedures, that is, (1) the combined use of lithium diisopropylamide and the chiral lithium amide 1b, (2) the use of an excess of the chiral lithium amide 1b, and (3) the regeneration of the chiral lithium amide 1b, afforded the aldol 4 in about 90% yield and 70% enantiomeric excess (ee). Investigation of the effects of solvent by utilizing 1-naphthaldehyde revealed that in tetrahydrofuran, (S, S)-aldol 5 of 77% ee was obtained as the major product, while in ether (R, R)-5 became the major isomer (38% ee). Furthermore, addition of hexamethylphosphoric triamide caused a dramatic change of stereoselectivity, and (S, S)-5 of 70% ee was obtained in ether with 20 eq of hexamethylphosphoric triamid. The aldol 4 of 74% ee was obtained when the new chiral lithium amide 6b was used.

Published
1991
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3. Phase-Transfer Catalysis

Author

MARC E. HALPERN, Charles M. Starks, Charles L. Liotta, Joachim Berkner, James Wright, Barbara Fair, M. Makosza, S. S. Yufit, G. V. Kryshtal, Irina A. Esikova, F. S. Sirovski, Theresa Stines Nahreini, Martin J. O'Donnell, Eckehard Volker Dehmlow, Aiqiao Mi, Daniel F. Shullenberger, Shengde Wu, Takayuki Shioiri, Akira Ando, Moriyasu Masui, Toshio Miura, Toshiaki Tatematsu, Akemi Bohsako, Masayo Higashiyama, Chiharu Asakura, Yoel Sasson, Noam Mushkin, Eli Abu, Samuel Negussie, Salman Dermeik, Ami Zoran, R. Roy, F. D. Tropper, S. Cao, J. M. Kim, Enrique Diez-Barra, Antonio de la Hoz, Sonia Merino, Prado Sánchez-Verdú, Toshio Takido, Takayoshi Fujihira, Manabu Seno, Kunio Itabashi, Yaozhong Jiang, Yuliang Wang, Runhua Deng, Tadatomi Nishikubo, Shigeo Nakamura, Chonghui Wang, Noritaka Ohtani, Yukihiko Inoue, Jun Mukudai, Tsuyoshi Yamashita, N. N. Dutta, A. C. Ghosh, R. K. Mathur, T. Balakrishnan, J. Paul Jayachandran, Mikio Ouchi, Kenji Mishima, Reizo Dohno, Tadao Hakushi, MARC E. HALPERN, Charles M. Starks, Charles L. Liotta, Joachim Berkner, James Wright, Barbara Fair, M. Makosza, S. S. Yufit, G. V. Kryshtal, Irina A. Esikova, F. S. Sirovski, Theresa Stines Nahreini, Martin J. O'Donnell, Eckehard Volker Dehmlow, Aiqiao Mi, Daniel F. Shullenberger, Shengde Wu, Takayuki Shioiri, Akira Ando, Moriyasu Masui, Toshio Miura, Toshiaki Tatematsu, Akemi Bohsako, Masayo Higashiyama, Chiharu Asakura, Yoel Sasson, Noam Mushkin, Eli Abu, Samuel Negussie, Salman Dermeik, Ami Zoran, R. Roy, F. D. Tropper, S. Cao, J. M. Kim, Enrique Diez-Barra, Antonio de la Hoz, Sonia Merino, Prado Sánchez-Verdú, Toshio Takido, Takayoshi Fujihira, Manabu Seno, Kunio Itabashi, Yaozhong Jiang, Yuliang Wang, Runhua Deng, Tadatomi Nishikubo, Shigeo Nakamura, Chonghui Wang, Noritaka Ohtani, Yukihiko Inoue, Jun Mukudai, Tsuyoshi Yamashita, N. N. Dutta, A. C. Ghosh, R. K. Mathur, T. Balakrishnan, J. Paul Jayachandran, Mikio Ouchi, Kenji Mishima, Reizo Dohno, and Tadao Hakushi

Subjects
Phase-transfer catalysis--Congresses
Published
1997

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