Chirale 1,3,2-Oxazaborolidine aus chiralen 2,3-Dihydro-1H-1,3,2-diazaborolen und Diphenylketen

Weber L, Rausch A, Stammler H-G, Neumann B (2005)
Zeitschrift für Anorganische und Allgemeine Chemie 631(9): 1633-1639.

Journal Article | Published | German

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Alternative Title
Chiral 1,3,2-oxazaborolidines from the reaction of chiral 2,3-dDihydro-1H-1,3,2-diazaboroles and diphenylketene
Abstract
Reaction of equimolar amounts of diphenylketene with 1,3-di-tert-butyl-2-isobutyl-2,3-dihydro-1H-1,3,2-diazaborole tBuNCH=CHN(tBu)B-iBu (1) regioselectively afforded 1,3,2-oxazaborolidine tBuN-CH(CH=NtBu)C(=CPh2)OB-iBu (2). The employment of a series of chiral diazaboroles (S,S)-Me(Cy)CHNCH=CH-N{CH(Cy)Me}BX (3a: X = nBu; b: nBu; c: CH2SiMe3; d: NHtBu) led to the formation of the diastereoisomeric oxazaborolidines Me(Cy)CHN-CH{CH=NCH(Cy)Me)C(=CPh2)OBX (4a-d) with diastereomeric excesses de, which increase with the steric demand of X from de = 55% (X = nBu) to de >= 95 % (X = NHtBu). Under comparable conditions the treatment of the enantiomerically pure diazaborole (S)-tBuNCH=CHN(tBu)B-NHCH Ph)Me (6) with the ketene yielded oxazaborolidine tBuNCH(CH= NtBu)C(=CPh2)OBNHCH(Ph)Me (7) with a de-value of only 52%. The new compounds, with exception of 2 and 4d, are thermolabile solids, which were characterized mainly by spectroscopy (H-1-, B-11(H-1}-,C-13{H-1}-NMR, MS). The X-ray structure analysis of 2 revealed a slightly puckered five-membered heterocycle with a long B-O bond.
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Weber L, Rausch A, Stammler H-G, Neumann B. Chirale 1,3,2-Oxazaborolidine aus chiralen 2,3-Dihydro-1H-1,3,2-diazaborolen und Diphenylketen. Zeitschrift für Anorganische und Allgemeine Chemie. 2005;631(9):1633-1639.
Weber, L., Rausch, A., Stammler, H. - G., & Neumann, B. (2005). Chirale 1,3,2-Oxazaborolidine aus chiralen 2,3-Dihydro-1H-1,3,2-diazaborolen und Diphenylketen. Zeitschrift für Anorganische und Allgemeine Chemie, 631(9), 1633-1639.
Weber, L., Rausch, A., Stammler, H. - G., and Neumann, B. (2005). Chirale 1,3,2-Oxazaborolidine aus chiralen 2,3-Dihydro-1H-1,3,2-diazaborolen und Diphenylketen. Zeitschrift für Anorganische und Allgemeine Chemie 631, 1633-1639.
Weber, L., et al., 2005. Chirale 1,3,2-Oxazaborolidine aus chiralen 2,3-Dihydro-1H-1,3,2-diazaborolen und Diphenylketen. Zeitschrift für Anorganische und Allgemeine Chemie, 631(9), p 1633-1639.
L. Weber, et al., “Chirale 1,3,2-Oxazaborolidine aus chiralen 2,3-Dihydro-1H-1,3,2-diazaborolen und Diphenylketen”, Zeitschrift für Anorganische und Allgemeine Chemie, vol. 631, 2005, pp. 1633-1639.
Weber, L., Rausch, A., Stammler, H.-G., Neumann, B.: Chirale 1,3,2-Oxazaborolidine aus chiralen 2,3-Dihydro-1H-1,3,2-diazaborolen und Diphenylketen. Zeitschrift für Anorganische und Allgemeine Chemie. 631, 1633-1639 (2005).
Weber, Lothar, Rausch, Andreas, Stammler, Hans-Georg, and Neumann, Beate. “Chirale 1,3,2-Oxazaborolidine aus chiralen 2,3-Dihydro-1H-1,3,2-diazaborolen und Diphenylketen”. Zeitschrift für Anorganische und Allgemeine Chemie 631.9 (2005): 1633-1639.
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