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Reference from the mechanism of 7+6 -> 8 found on p. 13067
Jung, M. E.; Ho, D.; Chu, H. V. Org. Lett. 2005, 7, 1649-1651.
In general this article is interested in the use of Lewis acid systems to catalyze highly substituted dienes and dienophiles to increase the yield of normally hindered Diels-Alder reactions.
1. Van Orden, L. J.; Patterson, B. D.; Rychnovsky, S. D. J. Org. Chem. 2007, 72, 5784-5793.
The overall experiment in Van Orden’s paper was observing the reaction of MAP with aldehydes and comparing the effect of various reaction conditions on the formation of the products. This paper cited Jung because in the experimental set up, the Lewis acid catalyst system described by Jung was used as one of the reaction conditions being tested.
2. Jung, M. E.; Ho, D. G. Org. Lett. 2006, 9, 375-378.
This article is the continuation on Jung’s publication in 2005. In this publication, the researchers explored the use of the Lewis acids used in Jung 2005 along with other catalysis to produce the product of the Diels alder reaction. By comparing the reaction schemes reported in this article in (2006) and those shown in the 2005 article, it appears that the researchers increased steric hindrance of the reaction using more substituted dienes by using TBS as an R group. Furthermore, they used their previously reported Lewis acid method combined with other reagents such as Tf2NH. Also, the lack of extensive citation of the Jung 2005 article may be due to these modifications explored in the 2006 paper and presumably subsequent publications improving the experimental procedure of increasing yield in highly substituted Diels alder reactions.
3. Jones, A. L.; Snyder, J. K. Org. Lett. 2010, 12, 1592-1595.
As pointed out previously, there is a lack of extensive use of the methods reported in Jung 2005 being used in other work. Most of articles citing Jung 2005 did so in reference to the generally unsuccessful research into an efficient method of activating a highly substituted Diels-Alder reaction. This reference by Jones is an example of the many articles that make this reference.
While a specific mechanism is not listed for this citing article, Jones cites Jung’s article to say that steric constraints generally prohibit intermolecular Diels-Alder reactions. This citing of the difficulties in working with highly substituted reagents is critical in her argument for the importance of her research which includes the use alternate methods to form the highly substituted cyclohexadienes to make them more reactive.
In general this article is interested in the use of Lewis acid systems to catalyze highly substituted dienes and dienophiles to increase the yield of normally hindered Diels-Alder reactions.
1. Van Orden, L. J.; Patterson, B. D.; Rychnovsky, S. D. J. Org. Chem. 2007, 72, 5784-5793.
The overall experiment in Van Orden’s paper was observing the reaction of MAP with aldehydes and comparing the effect of various reaction conditions on the formation of the products. This paper cited Jung because in the experimental set up, the Lewis acid catalyst system described by Jung was used as one of the reaction conditions being tested.
2. Jung, M. E.; Ho, D. G. Org. Lett. 2006, 9, 375-378.
This article is the continuation on Jung’s publication in 2005. In this publication, the researchers explored the use of the Lewis acids used in Jung 2005 along with other catalysis to produce the product of the Diels alder reaction. By comparing the reaction schemes reported in this article in (2006) and those shown in the 2005 article, it appears that the researchers increased steric hindrance of the reaction using more substituted dienes by using TBS as an R group. Furthermore, they used their previously reported Lewis acid method combined with other reagents such as Tf2NH. Also, the lack of extensive citation of the Jung 2005 article may be due to these modifications explored in the 2006 paper and presumably subsequent publications improving the experimental procedure of increasing yield in highly substituted Diels alder reactions.
3. Jones, A. L.; Snyder, J. K. Org. Lett. 2010, 12, 1592-1595.
As pointed out previously, there is a lack of extensive use of the methods reported in Jung 2005 being used in other work. Most of articles citing Jung 2005 did so in reference to the generally unsuccessful research into an efficient method of activating a highly substituted Diels-Alder reaction. This reference by Jones is an example of the many articles that make this reference.
While a specific mechanism is not listed for this citing article, Jones cites Jung’s article to say that steric constraints generally prohibit intermolecular Diels-Alder reactions. This citing of the difficulties in working with highly substituted reagents is critical in her argument for the importance of her research which includes the use alternate methods to form the highly substituted cyclohexadienes to make them more reactive.