Indium(I) bromide mediated coupling of α,α-dichloroketones with carbonyl compounds in aqueous media: The preparation of 2-chloro-3- hydroxypropan-1-one derivatives

Synlett

Volumn , Issue 4, 2006, Pages 605-609

  Peppe, Clovis ^a   Pavão Das Chagas, Rafael ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

2 chloro 3 hydroxypropan 1 one; Darzens condensation; Dichloroketones; Halogenomethyl indium(III); Indium(I) bromide

Indexed keywords

2 CHLORO 3 HYDROXYPROPAN 1 ONE DERIVATIVE; ACETONE; BROMINE DERIVATIVE; CARBONYL DERIVATIVE; INDIUM; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY;

EID: 33645004499     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-932479     Document Type: Article

References (17)

1. For discussion see: Peppe, C. Curr. Org. Synth. 2004, 1, 227.
2. Peppe, C.; das Chagas, R. P. Synlett 2004, 1187.
3. 3. For discussion of disproportionation of indium monohalides in presence of donnor ligands, see: Peppe, C.; Tuck, D. G.; Victoriano, L. J. Chem. Soc., Dalton Trans. 1982, 2165.
4. Podlech, J.; Maier, T. C. Synthesis 2003, 633.
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6. 2 (syn-2d) is deposited with the Cambridge Crystallographic Data Centre under the number CCDC 287226.
7. 2 (trans-3d) is deposited with the Cambridge Crystallographic Data Centre under the number CCDC 287227.
8. 35Cl): m/z (%) = 154 (10) [M], 105 (100), 77 (100), 51 (70).
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12. The authors also described the first successful aldol reaction between α,α-dichloroketones and aldehydes, catalyzed by samarium(III) hexamethyldisilazide, to produce 2,2-dichloro-3-hydroxypropan-1-one derivatives: Sasai, H.; Arai, S.; Shibasaki, M. J. Org. Chem. 1994, 59, 2661.
13. Tanabe, Y.; Matsumoto, N.; Higashi, T.; Misaki, T.; Itoh, T.; Yamamoto, M.; Mitarai, K.; Nishii, Y. Tetrahedron 2002, 58, 8269.
14. Araki, S.; Hirashita, T.; Shimizu, K.; Ikeda, T.; Butsugan, Y. Tetrahedron 1996, 52, 2803.
15. Compounds 2a-q were isolated from column chromatography as a mixture of diastereomers. We notice that the NMR data correspond to the major fraction containing the mixtute isolated by column chromatography. Therefore, they do not correspond to the diastereomeric ratio described in Table 1, which is the sum of all fractions containing the diastereomers.
16. Kitazume, T.; Jiang, Z.; Kasai, K.; Mihara, Y.; Suzuki, M. J. Fluorine Chem. 2003, 121, 205.
17. Kumaraswamy, G.; Sastry, M. N. V.; Jena, N.; Kumar, K. R.; Vairamani, M. Tetrahedron: Asymmetry 2003, 14, 3797.