The unexpected formation of trans-β-lactams in the reaction of α-iminoesters (R-N=C(H)C(=O)OR′) with diethylzinc. Crystal structure of trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxycarbonylazetidin-2-one

M. Robert P. van Vliet; J. T B H Jastrzebski; Wim J. Klaver; Kees Goubitz; Gerard van Koten

The unexpected formation of trans-β-lactams in the reaction of α-iminoesters (R-N=C(H)C(=O)OR′) with diethylzinc. Crystal structure of trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxycarbonylazetidin-2-one

M. Robert P. van Vliet, J. T B H Jastrzebski, Wim J. Klaver, Kees Goubitz, Gerard van Koten

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Reaction of iminoesters, R-N=C(H)COOR′, (R = t-Bu, i-Pr ; R′ = Me, Et ) with diethylzinc affords in a selective quantitative reaction trans-β-lactams. An X-ray crystal structure determination of the obtained trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxy-carbonylazetidin-2-one has been carried out. The formation of the trans-β-lactams is believed to proceed via zinc enolates.

Original language	English
Pages (from-to)	132-134
Number of pages	3
Journal	Recueil des Travaux Chimiques des Pays-Bas
Volume	106
Issue number	4
Publication status	Published - Apr 1987

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van Vliet, M. R. P., Jastrzebski, J. T. B. H., Klaver, W. J., Goubitz, K., & van Koten, G. (1987). The unexpected formation of trans-β-lactams in the reaction of α-iminoesters (R-N=C(H)C(=O)OR′) with diethylzinc. Crystal structure of trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxycarbonylazetidin-2-one. Recueil des Travaux Chimiques des Pays-Bas, 106(4), 132-134.

van Vliet, M. Robert P. ; Jastrzebski, J. T B H ; Klaver, Wim J. et al. / The unexpected formation of trans-β-lactams in the reaction of α-iminoesters (R-N=C(H)C(=O)OR′) with diethylzinc. Crystal structure of trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxycarbonylazetidin-2-one. In: Recueil des Travaux Chimiques des Pays-Bas. 1987 ; Vol. 106, No. 4. pp. 132-134.

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title = "The unexpected formation of trans-β-lactams in the reaction of α-iminoesters (R-N=C(H)C(=O)OR′) with diethylzinc. Crystal structure of trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxycarbonylazetidin-2-one",

abstract = "Reaction of iminoesters, R-N=C(H)COOR′, (R = t-Bu, i-Pr ; R′ = Me, Et ) with diethylzinc affords in a selective quantitative reaction trans-β-lactams. An X-ray crystal structure determination of the obtained trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxy-carbonylazetidin-2-one has been carried out. The formation of the trans-β-lactams is believed to proceed via zinc enolates.",

author = "{van Vliet}, {M. Robert P.} and Jastrzebski, {J. T B H} and Klaver, {Wim J.} and Kees Goubitz and {van Koten}, Gerard",

year = "1987",

month = apr,

language = "English",

volume = "106",

pages = "132--134",

journal = "Recueil des Travaux Chimiques des Pays-Bas",

issn = "0165-0513",

publisher = "Royal Netherlands Chemical Society",

number = "4",

}

van Vliet, MRP, Jastrzebski, JTBH, Klaver, WJ, Goubitz, K & van Koten, G 1987, 'The unexpected formation of trans-β-lactams in the reaction of α-iminoesters (R-N=C(H)C(=O)OR′) with diethylzinc. Crystal structure of trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxycarbonylazetidin-2-one', Recueil des Travaux Chimiques des Pays-Bas, vol. 106, no. 4, pp. 132-134.

The unexpected formation of trans-β-lactams in the reaction of α-iminoesters (R-N=C(H)C(=O)OR′) with diethylzinc. Crystal structure of trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxycarbonylazetidin-2-one. / van Vliet, M. Robert P.; Jastrzebski, J. T B H; Klaver, Wim J. et al.
In: Recueil des Travaux Chimiques des Pays-Bas, Vol. 106, No. 4, 04.1987, p. 132-134.

Research output: Contribution to journal › Article › Academic › peer-review

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T1 - The unexpected formation of trans-β-lactams in the reaction of α-iminoesters (R-N=C(H)C(=O)OR′) with diethylzinc. Crystal structure of trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxycarbonylazetidin-2-one

AU - van Vliet, M. Robert P.

AU - Jastrzebski, J. T B H

AU - Klaver, Wim J.

AU - Goubitz, Kees

AU - van Koten, Gerard

PY - 1987/4

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N2 - Reaction of iminoesters, R-N=C(H)COOR′, (R = t-Bu, i-Pr ; R′ = Me, Et ) with diethylzinc affords in a selective quantitative reaction trans-β-lactams. An X-ray crystal structure determination of the obtained trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxy-carbonylazetidin-2-one has been carried out. The formation of the trans-β-lactams is believed to proceed via zinc enolates.

AB - Reaction of iminoesters, R-N=C(H)COOR′, (R = t-Bu, i-Pr ; R′ = Me, Et ) with diethylzinc affords in a selective quantitative reaction trans-β-lactams. An X-ray crystal structure determination of the obtained trans-1-(N-t-butyl)-3-(N-t-butyl-N-ethylamino)-4-methoxy-carbonylazetidin-2-one has been carried out. The formation of the trans-β-lactams is believed to proceed via zinc enolates.

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M3 - Article

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