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New 2,5-diazabicyclo[2.2.1]heptanes and their application in the asymmetric addition of diethylzinc to benzaldehyde

Ulrich Jordis 1
Ulrich Jordis
, 
Martin Kesselgruber 1
Martin Kesselgruber
, 
Sven Nerdinger 1
Sven Nerdinger
, 
Kurt Mereiter 2
Kurt Mereiter
10.1070/MC1999v009n04ABEH001088
Published 1999-07-09
Communication , Volume 9, Issue 4, 147-148
8
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Jordis U. et al. New 2,5-diazabicyclo[2.2.1]heptanes and their application in the asymmetric addition of diethylzinc to benzaldehyde // Mendeleev Communications. 1999. Vol. 9. No. 4. pp. 147-148.
GOST all authors (up to 50) Copy
Jordis U., Kesselgruber M., Nerdinger S., Mereiter K. New 2,5-diazabicyclo[2.2.1]heptanes and their application in the asymmetric addition of diethylzinc to benzaldehyde // Mendeleev Communications. 1999. Vol. 9. No. 4. pp. 147-148.
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TY - JOUR
DO - 10.1070/MC1999v009n04ABEH001088
UR - https://mendcomm.colab.ws/publications/10.1070/MC1999v009n04ABEH001088
TI - New 2,5-diazabicyclo[2.2.1]heptanes and their application in the asymmetric addition of diethylzinc to benzaldehyde
T2 - Mendeleev Communications
AU - Jordis, Ulrich
AU - Kesselgruber, Martin
AU - Nerdinger, Sven
AU - Mereiter, Kurt
PY - 1999
DA - 1999/07/09
PB - Mendeleev Communications
SP - 147-148
IS - 4
VL - 9
ER -
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@article{1999_Jordis,
author = {Ulrich Jordis and Martin Kesselgruber and Sven Nerdinger and Kurt Mereiter},
title = {New 2,5-diazabicyclo[2.2.1]heptanes and their application in the asymmetric addition of diethylzinc to benzaldehyde},
journal = {Mendeleev Communications},
year = {1999},
volume = {9},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1999v009n04ABEH001088},
number = {4},
pages = {147--148},
doi = {10.1070/MC1999v009n04ABEH001088}
}
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Jordis, Ulrich, et al. “New 2,5-diazabicyclo[2.2.1]heptanes and their application in the asymmetric addition of diethylzinc to benzaldehyde.” Mendeleev Communications, vol. 9, no. 4, Jul. 1999, pp. 147-148. https://mendcomm.colab.ws/publications/10.1070/MC1999v009n04ABEH001088.

Abstract

New (1S,4S)-2,5-diazabicyclo[2.2.1]heptane derivatives synthesised by directed ortho metalation result in enantioselectivities of up to 78% e.e. when used as catalysts in the addition of diethylzinc to benzaldehyde.

References

10.
Enantioselective synthesis via sparteine-induced asymmetric deprotonation
Hoppe D., Hintze F., Tebben P., Paetow M., Ahrens H., Schwerdtfeger J., Sommerfeld P., Haller J., Guarnieri W., Kolczewski S., Hense T., Hoppe I.
Pure and Applied Chemistry, 1994
11.
Synthesis of (S,S)- and (R,R)-2-alkyl-2,5-diazabicyclo[2.2.1]heptanes
Braish T.F., Fox D.E.
Journal of Organic Chemistry, 1990