Synthesis of C1-symmetric primary-secondary diamines and their application in the enantioselective Henry reaction
Two new C 1 -symmetric primary-secondary diamines were synthesized via the reaction of ( S,S )-1,2-diphenyl ethylene diamine with 3,5-ditert-butyl salicylaldehyde and salicylaldehyde, respectively, followed by reduction with NaBH 4 . The combination of the ligand from 3,5-ditert-butyl salicylaldehyd...
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Published in | Frontiers of chemical science and engineering Vol. 7; no. 4; pp. 408 - 414 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Berlin/Heidelberg
Springer Berlin Heidelberg
01.12.2013
|
Subjects | |
Online Access | Get full text |
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Summary: | Two new
C
1
-symmetric primary-secondary diamines were synthesized via the reaction of (
S,S
)-1,2-diphenyl ethylene diamine with 3,5-ditert-butyl salicylaldehyde and salicylaldehyde, respectively, followed by reduction with NaBH
4
. The combination of the ligand from 3,5-ditert-butyl salicylaldehyde with CuBr could effciently catalyze the Henry reaction to afford
β
-nitroalkanols in moderate to good yields (up to 87%) and high enantioselectivities (up to 88%
ee
). A possible mechanism of the reaction was proposed. |
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ISSN: | 2095-0179 2095-0187 |
DOI: | 10.1007/s11705-013-1343-4 |