Czasopismo
Tytuł artykułu
Autorzy
Warianty tytułu
Języki publikacji
Abstrakty
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.
Czasopismo
Rocznik
Tom
Numer
Opis fizyczny
Daty
otrzymano
2015-05-05
zaakceptowano
2015-06-09
online
2015-06-29
Twórcy
autor
-
Departamento de
Química, Centro de Investigación y de Estudios Avanzados, Instituto
Politécnico Nacional, Apartado Postal 14-740, 07000-México D.F.
(Mexico)
autor
-
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)
autor
-
Departamento de
Química, Centro de Investigación y de Estudios Avanzados, Instituto
Politécnico Nacional, Apartado Postal 14-740, 07000-México D.F.
(Mexico)
autor
-
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)
autor
-
Departamento de
Química, Centro de Investigación y de Estudios Avanzados, Instituto
Politécnico Nacional, Apartado Postal 14-740, 07000-México D.F.
(Mexico)
Bibliografia
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Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_1515_asorg-2015-0004