Pinane-type tridentate reagents for enantioselective reactions: Reduction of ketones and addition of diethylzinc to aldehydes

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 3207-3212

  Cherng, Yie Jia ^a,c   Fang, Jim Min ^a   Lu, Ta Jung ^b  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^c CHUNGTAI INST HLTH SCI TECHNOL   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

10 ANILINO 3 ETHOXY 2 HYDROXYPINANE; 10 BUTYLANILINO 2,3 DIHYDROXYPINANE; ACETOPHENONE; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; RACEMIC MIXTURE; REDUCTION; STEREOCHEMISTRY;

EID: 0033617139     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982403b     Document Type: Article

References (60)

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25. Analogous transition states in asymmetric LAH reductions using aminodiol or diamino alcohol tridentate modifiers have been proposed. (a) Morrison, J. D.; Grandbois, E. R.; Howard, S. I.; Weisman, G. R. Tetrahedron Lett. 1981, 22, 2619. (b) Sato, T.; Goto, Y.; Fujisawa, T. Tetrahedron Lett. 1982, 23, 4111. Similar transition states in the reactions of organolithiums: (c) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455. (d) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (e) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624.
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38. 2Zn additions using terpenic amino alcohol promoters: (l) Masui, M.; Shioiri, T. Synlett 1997, 273. (m) Goralski, C. T.; Chrisman, W.; Hasha, D. L.; Nicholson, L. W.; Rudolf, P. R.; Zakett, D.; Singaram, B. Tetrahedron: Asymmetry 1997, 8, 3863. (n) Genov, M.; Dimitrov, V.; Ivanova, V. Tetrahedron: Asymmetry 1997, 8, 3703.
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43. 2Zn additions using terpenic amino alcohol promoters: (l) Masui, M.; Shioiri, T. Synlett 1997, 273. (m) Goralski, C. T.; Chrisman, W.; Hasha, D. L.; Nicholson, L. W.; Rudolf, P. R.; Zakett, D.; Singaram, B. Tetrahedron: Asymmetry 1997, 8, 3863. (n) Genov, M.; Dimitrov, V.; Ivanova, V. Tetrahedron: Asymmetry 1997, 8, 3703.
44. 2Zn additions using terpenic amino alcohol promoters: (l) Masui, M.; Shioiri, T. Synlett 1997, 273. (m) Goralski, C. T.; Chrisman, W.; Hasha, D. L.; Nicholson, L. W.; Rudolf, P. R.; Zakett, D.; Singaram, B. Tetrahedron: Asymmetry 1997, 8, 3863. (n) Genov, M.; Dimitrov, V.; Ivanova, V. Tetrahedron: Asymmetry 1997, 8, 3703.
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