Catalytic asymmetric homo-aldol reaction of pyruvate—a chiral Lewis acid catalyst that mimics aldolase enzymes
作者： Karsten Juhl , Nicholas Gathergood , Karl Anker Jørgensen
DOI: 10.1039/B007125K
关键词:
摘要: The first catalytic asymmetric homo-aldol reaction of ethyl pyruvate leading to diethyl-2-hydroxy-2-methyl-4-oxoglutarate in up 96% enantiomeric excess is reported; this has been investigated for various catalysts, amines and solvents, it demonstrated that new leads a simple synthetic procedure the formation optically active isotetronic acid derivatives.
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Koichi Mikami, Satoru Matsukawa, Asymmetric Catalytic Aldol-type Reaction with Ketene Silyl Acetals: Possible Intervention of the Silatropic Ene Pathway Journal of the American Chemical Society. ,vol. 116, pp. 4077- 4078 ,(1994) , 10.1021/JA00088A053
Wheeseong Lee, Robert A. Singer, Erick M. Carreira, Catalytic, Enantioselective Acetone Aldol Additions with 2-Methoxypropene Journal of the American Chemical Society. ,vol. 117, pp. 3649- 3650 ,(1995) , 10.1021/JA00117A049
TAKAYUKI NAMIKI, YUKIHISA BABA, YASUTAKA SUZUKI, MOTOAKI NISHIKAWA, KOZO SAWADA, YOSHIKUNI ITOH, TERUO OKU, YOSHIHIKO KITAURA, MASASHI HASHIMOTO, Synthesis and aldose reductase-inhibitory activities of structural analogues of WF-3681, a novel aldose reductase inhibitor. Chemical & Pharmaceutical Bulletin. ,vol. 36, pp. 1404- 1414 ,(1988) , 10.1248/CPB.36.1404
T. Keith Hollis, B. Bosnich, HOMOGENEOUS CATALYSIS. MECHANISMS OF THE CATALYTIC MUKAIYAMA ALDOL AND SAKURAI ALLYLATION REACTIONS Journal of the American Chemical Society. ,vol. 117, pp. 4570- 4581 ,(1995) , 10.1021/JA00121A015
Joaquim Bigorra, Josep Font, Cristina Ochoa de Echagüen, Rosa M. Ortuño, Synthetic approaches to either homochiral or achiral derivatives of 3-hydroxy-2(5H)-furanone (isotetronic acid) Tetrahedron. ,vol. 49, pp. 6717- 6728 ,(1993) , 10.1016/S0040-4020(01)81841-X
Erick M. Carreira, Robert A. Singer, Wheeseong Lee, Catalytic, Enantioselective Aldol Additions with Methyl and Ethyl Acetate O-Silyl Enolates: A Chiral Tridentate Chelate as a Ligand for Titanium(IV) Journal of the American Chemical Society. ,vol. 116, pp. 8837- 8838 ,(1994) , 10.1021/JA00098A065
Kaori Ishimaru, Keiji Monda, Yohsuke Yamamoto, Kin-ya Akiba, Novel cationic titanium(IV) Lewis acids and their use in asymmetric aldol reactions Tetrahedron. ,vol. 54, pp. 727- 734 ,(1998) , 10.1016/S0040-4020(97)10296-4
Itsuo Uchida, Yoshikuni Itoh, Takayuki Namiki, Motoaki Nishikawa, Masashi Hashimoto, Structure and synthesis of WF 3681, a novel aldose reductase inhibitor Tetrahedron Letters. ,vol. 27, pp. 2015- 2018 ,(1986) , 10.1016/S0040-4039(00)84436-6
David A. Evans, Marisa C. Kozlowski, Jerry A. Murry, Christopher S. Burgey, Kevin R. Campos, Brian T. Connell, Richard J. Staples, C2-Symmetric Copper(II) Complexes as Chiral Lewis Acids. Scope and Mechanism of Catalytic Enantioselective Aldol Additions of Enolsilanes to (Benzyloxy)acetaldehyde Journal of the American Chemical Society. ,vol. 121, pp. 669- 685 ,(1999) , 10.1021/JA9829822
Yuntae Kim, Robert A. Singer, Erick M. Carreira, Total Synthesis of Macrolactin A with Versatile Catalytic, Enantioselective Dienolate Aldol Addition Reactions Angewandte Chemie International Edition. ,vol. 37, pp. 1261- 1263 ,(1998) , 10.1002/(SICI)1521-3773(19980518)37:9<1261::AID-ANIE1261>3.0.CO;2-2