Highly stereoselective hydrocyanation of optically pure α- sulfinylaldehydes

Tetrahedron Asymmetry

Volumn 9, Issue 5, 1998, Pages 859-864

  Cifuentes García, Marta M ^a   García Ruano, José Luis ^a   Martín Castro, Ana M ^a   Rodríguez Ramos, Jesús H ^a   Fernández, Inmaculada ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXYAMIDE DERIVATIVE; ALPHA SULFINYLALDEHYDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DESULFURIZATION; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032513159     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00026-3     Document Type: Article

References (19)

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2. 1. Smitskamp-Wilms, E.; Brussee, J.; van der Gen, A. Rec. Trav. Chim. Pays-Bas 1991, 110, 209. Aketa, K.; Ohno, N.; Itaya, N.; Nakayama, I.; Yoshioka, H. Agric. Biol. Chem. 1978, 42, 895. Arit, D.; Jautelat, M.; Lantzsch, R. Angew. Chem., Int. Ed. Engl. 1981, 20, 703.
3. 1. Smitskamp-Wilms, E.; Brussee, J.; van der Gen, A. Rec. Trav. Chim. Pays-Bas 1991, 110, 209. Aketa, K.; Ohno, N.; Itaya, N.; Nakayama, I.; Yoshioka, H. Agric. Biol. Chem. 1978, 42, 895. Arit, D.; Jautelat, M.; Lantzsch, R. Angew. Chem., Int. Ed. Engl. 1981, 20, 703.
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12. 5. The previously described procedure (Ref. 4) for the synthesis of 1 uses a 1.0:1.1:1.1 sulfoxide:base:N-formylpiperidine ratio. We have used a 1.0:1.1:0.5 ratio in order to avoid the presence of N-formylpiperidine which contaminates the reaction product, since it was not possible to eliminate it either in this step or in a further one. Under these conditions a mixture of the corresponding aldehyde 1 or 2 and the unchanged alkyl (methyl or ethyl) p-tolyl sulfoxide was obtained. All attempts to isolate pure aldehyde by chromatography (either with silica gel or alumina) were unsuccessful. Hence, these mixtures were used as the starting material in further reactions. The resulting excess of unchanged sulfoxide can be easily removed in the following step. Difficulties in the purification of α-sulfinylaldehydes may be responsible for the fact that despite the synthesis of compound 1 described in 1988 (Ref. 4), to our knowledge this work is the first application of this compound in asymmetric synthesis so far reported in the literature.
13. 6. Previously it had been reported that α-sulfinylacetaldehyde 1 could not be prepared due to its instability (Banfi, L.; Colombo, L.; Gennari, C. Synthesis 1982, 829).
14. 7. García Ruano, J. L.; Martín Castro, A. M.; Rodríguez Ramos, J. H. Tetrahedron Lett. 1996, 37, 4569.
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16. 8. See: Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed., Academic Press: New York, 1983, Vol. 1, p. 125. Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
17. 8. See: Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed., Academic Press: New York, 1983, Vol. 1, p. 125. Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
18. 9. Butlin, R. J.; Linney, I. D.; Mahon, M. F.; Tye, H.; Wills, M. J. Chem. Soc., Perkin Trans. 1, 1996, 95. Nishide, K.; Shigeta, Y.; Obata, K.; Inoue, T.; Node, M. Tetrahedron Lett. 1996, 37, 2271.
19. 9. Butlin, R. J.; Linney, I. D.; Mahon, M. F.; Tye, H.; Wills, M. J. Chem. Soc., Perkin Trans. 1, 1996, 95. Nishide, K.; Shigeta, Y.; Obata, K.; Inoue, T.; Node, M. Tetrahedron Lett. 1996, 37, 2271.