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2015 | 2 | 1 |
Article title

Use of (R)-Mandelic Acid as Chiral Co-Catalyst in
the Michael Addition Reaction Organocatalyzed
by (1S,4S)-2-Tosyl-2,5-diazabicyclo[2.2.1]heptane
under Solvent-Free Conditions

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EN
Abstracts
EN
This article describes a study on the Michael
addition reaction of cyclohexanone to nitroolefins
catalyzed by the chiral secondary amine (1S,4S)-2-tosyl-
2,5-diazabicyclo[2.2.1]heptane. Reactions were carried
out under solvent-free conditions to make them more
environmentally friendly. Initially, the observed diastereoand
enantioselectivities were moderate to good, but
were significantly improved by lowering the reaction
temperature. Furthermore, a variety of chiral acids were
also tested as co-catalysts in both of their enantiomeric
forms, which revealed that (R)-mandelic acid affords
excellent results in terms of yield and stereoselectivity.
Monitoring the reaction by MS-TOF allowed for the
detection of key reaction intermediates, and a reasonable
reaction mechanism in which both catalysts are involved
is proposed.
Publisher
Year
Volume
2
Issue
1
Physical description
Dates
online
29 - 6 - 2015
received
5 - 5 - 2015
accepted
9 - 6 - 2015
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Document Type
Publication order reference
YADDA identifier
bwmeta1.element.-psjd-doi-10_1515_asorg-2015-0004
Identifiers
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