The steric effect and enantioselectivity of chiral 2,2-disubstituted thiaprolinol derivatives as ligands for borane reduction of aromatic ketones and for diethylzinc addition to aromatic aldehydes

Tetrahedron Asymmetry

Volumn 7, Issue 11, 1996, Pages 3067-3070

  Huang, Hsiang Ling ^a   Lin, Ya Chuan ^a   Chen, Shyh Fong ^a   Wang, Chia Lin J ^a   Liu, Lee Tai ^a  

^a DEVELOPMENT CENTER FOR BIOTECHNOLOGY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION;

EID: 0030575848     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00399-0     Document Type: Article

References (20)

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3. (c) Deloux, L.; Srebnik, M. Chem. Rev. 1993. 93, 763.
4. (2) Recent reviews of enantioselective addition of dialkylzinc to aldehydes: (a) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49.
5. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
6. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994; Chapter 5.
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10. (b) Mathre, D.; Thompson, A. S.; Douglas, A. W.; Hoogsteen, K.; Carrol, J. D.; Corley, E. G.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 2880.
11. (5) Acyclic sulfur-containing chiral amino alcohols: (a) Mehker, T.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 1983.
12. (b) Mehker, T.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 2299.
13. Serine and threonine derived chiral amino alcohols: (c) Falorni, M.; Collu, C.; Sandra, C.; Giacomelli, G. Tetrahedron: Asymmetry 1996, 7, 293.
14. 3).
15. (7) We found no significant enantioselectivity if the reduction was performed at lower temperature, also see: Jiang, Y.; Qin, Y.; Mi, A. Tetrahedron: Asymmetry 1994, 5, 1211.
16. (8) (a) Corey, E. J.; Azimioara, M.; Sarshar, S. Tetrahedron Lett. 1992, 33, 3429.
17. (b) Kim, Y. H.; Park, D. H.; Byun, I. S. J. Org. Chem. 1993, 58, 4511.
18. (9) (a) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111.
19. (b) Corey, E. J.; Yuen, P.-W.; Hannon, F.; Wierda, D. A. J. Org. Chem. 1990, 55, 784.
20. (10) We thank Ms. Ying Chen for operating NMR spectrometers.