Diastereoselektive Synthese von 1,3,2-Oxazaborolidinen aus chiralen 1,3,2-Diazaborolen

Rausch A (2005)
Bielefeld (Germany): Bielefeld University.

Download
OA
Bielefeld Dissertation | German
Author
Supervisor
Alternative Title
Diastereoselective synthesis of 1,3,2-oxazaborolidines from chiral 1,3,2-diazaboroles
Abstract
Ausgehend von chiralen primären Aminen wurde eine Reihe chiraler 2,3-Dihydro-1H-1,3,2-diazaborole dargestellt. Die Reaktion dieser Verbindungen mit äquimolaren Mengen Diphenylketen führt zur Bildung von chiralen 1,3,2-Oxazaborolidinen. Die chiralen Diazaborole (S,S)-Me(Cy)CH-N*CH=CH-N{CH(Cy)Me}B*-X (N*-B*, 15b: X = nBu; 20b: iBu; 21b: CH2SiMe3; 11b:NHtBu) zeigten Umsetzungen zu den diastereomeren Oxazaborolidinen mit Ausbeuten von 70 - 98 Prozent und einen mit dem sterischen Anspruch des Substituenten X ansteigenden Diastereomerenüberschuss (de) von 55 Prozent (X = nBu) bis 95 Prozent (X = NHtBu).

By use of chiral primary amines a series of differently substituted chiral 2,3-dihydro-1H-1,3,2-diazaboroles has been prepared by various methods. Reaction of equimolar amounts of diphenylketene afforded chiral 1,3,2-oxazaborolidines. The employment of a series of chiral diazaboroles (S,S)-Me(Cy)CH-N*CH=CH-N{CH(Cy)Me}B*-X (N*-B*, 15b: X = nBu; 20b: iBu; 21b: CH2SiMe3; 11b: NHtBu) led to the formation of the diastereoisomeric oxazaborolidines Me(Cy)CHN*-CH{CH=NCH(Cy)Me}C(=CPh2)OB*X (N*-B*, 150b, 200b, 210b, 110b) in yields of 70 - 98 percent with diastereomeric excesses de, which increase with the steric demand of X from de = 55 percent (X = nBu) to de = 95 percent (X = NHtBu).
Year
PUB-ID

Cite this

Rausch A. Diastereoselektive Synthese von 1,3,2-Oxazaborolidinen aus chiralen 1,3,2-Diazaborolen. Bielefeld (Germany): Bielefeld University; 2005.
Rausch, A. (2005). Diastereoselektive Synthese von 1,3,2-Oxazaborolidinen aus chiralen 1,3,2-Diazaborolen. Bielefeld (Germany): Bielefeld University.
Rausch, A. (2005). Diastereoselektive Synthese von 1,3,2-Oxazaborolidinen aus chiralen 1,3,2-Diazaborolen. Bielefeld (Germany): Bielefeld University.
Rausch, A., 2005. Diastereoselektive Synthese von 1,3,2-Oxazaborolidinen aus chiralen 1,3,2-Diazaborolen, Bielefeld (Germany): Bielefeld University.
A. Rausch, Diastereoselektive Synthese von 1,3,2-Oxazaborolidinen aus chiralen 1,3,2-Diazaborolen, Bielefeld (Germany): Bielefeld University, 2005.
Rausch, A.: Diastereoselektive Synthese von 1,3,2-Oxazaborolidinen aus chiralen 1,3,2-Diazaborolen. Bielefeld University, Bielefeld (Germany) (2005).
Rausch, Andreas. Diastereoselektive Synthese von 1,3,2-Oxazaborolidinen aus chiralen 1,3,2-Diazaborolen. Bielefeld (Germany): Bielefeld University, 2005.
Main File(s)
Access Level
OA Open Access

This data publication is cited in the following publications:
This publication cites the following data publications:

Export

0 Marked Publications

Open Data PUB

Search this title in

Google Scholar