2006
DOI: 10.1021/ja061152i
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Functionalized Chiral Vinyl Aminosulfoxonium Salts:  Asymmetric Synthesis and Application to the Synthesis of Enantiopure Unsaturated Prolines, β,γ-Dehydro Amino Acids, and Cyclopentanoid Keto Aminosulfoxonium Ylides

Abstract: Methylation of the enantiopure functionalized vinyl sulfoximines 5a-e and 14a-d followed by a F- ion or DBU-mediated isomerization of the vinyl aminosulfoxonium salts 7a-e and 15a-d, respectively, gave the allyl aminosulfoxonium salts 10a-e and 17a-d, respectively. A concomitant intramolecular substitution of the aminosulfoxonium group of 10a-e and 17a-d by the amino group afforded the unsaturated prolines 8a-e and 18a-d, respectively. The starting vinyl sulfoximines are accessible through a highly selective a… Show more

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Cited by 49 publications
(26 citation statements)
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“…In 1980 Johnson’s group demonstrated that vinylsulfoxonium salts could undergo conjugate addition reactions with a range of protic nucleophiles (some ambident), including amines, ketoesters, and nitromethane to afford 3-membered and 5-membered cyclic products [ 21 ]. However, vinylsulfoxonium salt research remained largely dormant until Gais’s group carried out further work in the 1990s and 2000s [ 22 , 23 , 24 ]. On the other hand, vinylsulfoniums have attracted a lot of interest recently, in no small part, due to the contributions of the Aggarwal group in the period 2000 to present [ 25 ].…”
Section: Early Contributionsmentioning
confidence: 99%
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“…In 1980 Johnson’s group demonstrated that vinylsulfoxonium salts could undergo conjugate addition reactions with a range of protic nucleophiles (some ambident), including amines, ketoesters, and nitromethane to afford 3-membered and 5-membered cyclic products [ 21 ]. However, vinylsulfoxonium salt research remained largely dormant until Gais’s group carried out further work in the 1990s and 2000s [ 22 , 23 , 24 ]. On the other hand, vinylsulfoniums have attracted a lot of interest recently, in no small part, due to the contributions of the Aggarwal group in the period 2000 to present [ 25 ].…”
Section: Early Contributionsmentioning
confidence: 99%
“…Gais and co-workers extended their study on the asymmetric synthesis of proline derivatives 146 after they reported the formation of unsaturated bicyclic prolines 129 [ 22 ]. They applied a similar strategy but this time employing a F − ion-mediated migratory cyclization rather than DBU, to deliver the desired monocyclic 3,4-unsaturated prolines 146 with ≥98% ee and in moderate to excellent yields ( Scheme 47 ) [ 24 ]. The vinyl aminosulfoxonium salts 145 subjected to cyclization in the three-phase system were prepared by activation of the corresponding chiral vinylsulfoximines 144 through methylation with Meerwein’s salt.…”
Section: Reactions Of Vinylsulfoxonium Saltsmentioning
confidence: 99%
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