Stereoselective one-pot synthesis of β-lactams by Lewis acid promoted condensation of silylketene thioacetals with imines

Tetrahedron

Volumn 52, Issue 7, 1996, Pages 2573-2582

  Annunziata, Rita ^a   Cinquini, Mauro ^a   Cozzi, Franco ^a   Molteni, Valentina ^a   Schupp, Olaf ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030038998     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01083-1     Document Type: Article

References (60)

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8. For leading references to the preparation of trichlorotitanium enolates see: Evans, D.A.; Bilodeau, M.T.; Somers, T.C.; Clardy, J.; Cherry, D.; Kato, Y. J. Org. Chem. 1991, 56, 5750, and references therein.
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15. Zr and Al 2-pyridylthioester enolates are also effective in this reaction: unpublished results from these laboratories.
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17. a) Hirai, K.; Homma, H.; Mikoshiba, I. Heterocycles 1994, 38, 281. In this paper, some reactions of compounds 11 and 14 with N-arylbenzaldimines are described, but no details on the synthesis of 11 and 14, or on their physical and spectroscopic properties are reported,
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21. Gennari, C. in Comprehensive Organic Synthesis vol. 2, part 2; Trost, B.; Fleming, I.; Heathcock, C.H., Ed.; Pergamon Press: Oxford 1991; pp 629-660.
22. LA promoted silylketene acetals addition to imines generally afford β-aminoesters. See for instance: a) Ojima, I.; Inaba, S.; Yoshida, K. Tetrahedron Lett. 1977, 18, 3643.
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30. i) Colvin, E.W.; McGarry, D.G.; Nugent, M.J. Tetrahedron 1988, 44, 4157.
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41. t) Shimizu, M.; Kuma, K.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 5227. Only in three cases this approach afforded β-lactams in a one-pot procedure:
42. u) Ojima, I.; Inaba, S. Tetrahedron Lett. 1980, 21, 2077, 2081.
43. v) Dubois, J.-E.; Axiotis, G.Tetrahedron Lett. 1984, 25, 2143. See also ref 8a.
44. NOE experiments have been previously exploited to assign the double bond configuration of some silylketene acetals derived from phenylacetates: a) Tanaka, F.; Fuji, K. Tetrahedron Lett. 1992, 33, 7885.
45. b) Corset, J.; Froment, F.; Lautie', M.-F.; Ratovelomanana, N.; Seyden-Penne, J.; Strzalko, T.; Roux-Schmitt, M.-C. J. Am. Chem. Soc. 1993, 115, 1684.
46. c) Solladie'-Cavallo, A.; Csaky, A.G. J. Org. Chem. 1994, 59, 2585.
47. For compounds 14-16 a NOE was observed between the vinyl proton and the proton at C-3 on the pyridine ring. This observation suggests that these SKTA adopt the so called "pin-wheel" conformation, as proposed for other silylketene acetals by: Wilcox, C.S.; Babston, R.E. J. Org. Chem. 1984, 49, 1451. The existence of this conformation has been demonstrated by X-rays in the case of the silylketene acetal derived from t-butylpropionate: Babston, R.E.; Lynch, V.; Wilcox, C.S. Tetrahedron Lett. 1989, 30, 447.
48. For compounds 14-16 a NOE was observed between the vinyl proton and the proton at C-3 on the pyridine ring. This observation suggests that these SKTA adopt the so called "pin-wheel" conformation, as proposed for other silylketene acetals by: Wilcox, C.S.; Babston, R.E. J. Org. Chem. 1984, 49, 1451. The existence of this conformation has been demonstrated by X-rays in the case of the silylketene acetal derived from t-butylpropionate: Babston, R.E.; Lynch, V.; Wilcox, C.S. Tetrahedron Lett. 1989, 30, 447.
49. By analogy with 14-16 the (E) configuration was assigned also to compound 13. This assignment is in agreement with that of Hirai, et al. (ref.7), that used the (Z) descriptor for (E) 13.
50. 1H NMR analysis of the crude reaction mixtures. The assignment resided on the value of the β-lactam HC-3/HC-4 coupling constant (J trans = 2.0-2.5 Hz; J cis = 5.0-6.0 Hz).
51. In this case the use of 2.0 mol. equiv. of LA gave better results (see entries 10-12, Table 2).
52. SKTA 17 and 18 were shown to be configurationally stable at 0°C in the dark in the presence of TBDMSOTf, thus showing that the LA does not promote (E)/(Z) isomerization.
53. For an anologous observation on the different reactivity of related SKTA see: Kobayashi, S.; Horibe, M.; Hachiya, I. Tetrahedron Lett. 1995, 36, 3173; and references cited therein.
54. For leading references to the concept of chelation see: Reetz, M.T. Acc. Chem. Res. 1993, 26, 462.
55. Imines of aromatic aldehydes are known to exist and react in the (E) configuration, while those of aliphatic aldehydes generally exist as mixtures of (E) and (Z) isomers. For a review see: McCarty, C.G. in: "The Chemistry of the C-N Double Bond", Patai, S.; Ed.; Interscience, New York, 1970; chapter 9, pp 363-464. Aromatic imines such as 21 and 28 were shown not to isomerize even in the presence of strong LA (see ref. 1 and 4).
56. Antiperiplanar transition states have been found to be preferred over their synclinal counterparts in a intramolecular LA catalyzed aldol condensation: Denmark, S.E.; Lee, W. J. Org. Chem. 1994, 59, 707.
57. Models analogous to A and B are generally used to explain the simple anti stereoselectivity of Mukaiyama aldol condensations (see ref.9). For instance, they have been recently propose to rationalize the LA promoted addition of SKTA 13 to benzaldehyde (see ref.Sb).
58. 4 was added to SKTA 13 the signals of the pyridine hydrogens were shifted downfield as follows: HC-3 from 7.23 to 7.86 ppm; HC-4 from 7.54 to 8.22 ppm; HC-5 from 6.98 to 7.72 ppm; HC-6 from 8.41 to 8.80 ppm. The Me and vinyl proton signals remained unchanged, as did the spectrum of the mixture after 3 h at 0°C. Thus, in these conditions neither a titanium enolate (ref. 1) is formed, nor SKTA 13 isomerizes.
59. 3/N-methylephedrine adduct. The configuration of optically active 22t and 22c has been determined as described in ref. 4b.
60. Kobayashi, S.; Iimori, T.; Izawa, T.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 2406.