Asymmetric catalysis of Nozaki-Hiyama allylation and methallylation with a new tridentate bis(oxazolinyl)carbazole ligand

Journal of the American Chemical Society

Volumn 125, Issue 5, 2003, Pages 1140-1141

  Inoue, Masahiro ^a   Suzuki, Takahiro ^a   Nakada, Masahisa ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; CARBAZOLE DERIVATIVE; CHLORIDE; TRIDENTATE BIS(OXAZOLINYL)CARBAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL BINDING; COMPLEX FORMATION; ENANTIOSELECTIVITY; METHYLATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037419886     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021243p     Document Type: Article

References (41)

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18. See Supporting Information for the preparation of 1.
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20. 2-symmetrical tridentate ligands, for pybox: (a) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846-848. For DBFOX: (b) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454-6455. Unfortunately, satisfactory results for the enantioselective Nozaki-Hiyama allylations were not obtained with these ligands.
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23. N-ethylpiperidine, triethylamine, and tri-n-butylamine were also effective for this highly enantioselective reaction, but the yields were slightly lowered.
24. For experimental procedure, see Supporting Information.
25. Low temperature (0 °C) did not increase the enantioselectivity in other reactions except entry 7.
26. 2 and ligand 1, the allylated products were obtained in 8 and 14% yield under the conditions of entries 2 and 7, respectively. Aliphatic aldehydes are surmised to be rather inert to allylmanganase reagent. Cf. ref 3.
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29. 2 (20 mol %), ent-ligand 1 (20 mol %), Mn (4.0 equiv), methallyl chloride (2.0 equiv), and DIPEA (1.0 equiv) were used. Without entligand 1, the reaction proceeded sluggishly. The details will be communicated.
30. Characterization of the recovered Cr-ligand 1 complex is now under investigation.
31. The same condition for the enantioselective allylation was used.
32. 1H NMR and HPLC of Mosher's ester of 7; see ref 4e. Yields were the combined yield.
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41. An additional interesting feature of this reaction is that no pinacol product (cf. ref 4) was found in the all reactions reported here.