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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

Content

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Languages of publication

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

Contributors

  • Departamento de
    Química, Centro de Investigación y de Estudios Avanzados, Instituto
    Politécnico Nacional, Apartado Postal 14-740, 07000-México D.F.
    (Mexico)
  • Facultad de Estudios Superiores
    Zaragoza, Universidad Nacional Autónoma de México (UNAM),
    Batalla del 5 de Mayo y Fuerte de Loreto, Iztapalapa, 09230, México,
    D.F. (Mexico)
  • Departamento de
    Química, Centro de Investigación y de Estudios Avanzados, Instituto
    Politécnico Nacional, Apartado Postal 14-740, 07000-México D.F.
    (Mexico)
author
  • Facultad de Estudios Superiores
    Zaragoza, Universidad Nacional Autónoma de México (UNAM),
    Batalla del 5 de Mayo y Fuerte de Loreto, Iztapalapa, 09230, México,
    D.F. (Mexico)
  • Departamento de
    Química, Centro de Investigación y de Estudios Avanzados, Instituto
    Politécnico Nacional, Apartado Postal 14-740, 07000-México D.F.
    (Mexico)

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Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_1515_asorg-2015-0004
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