| 1. |
- Kamlar, Martin, 1981, et al.
(författare)
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Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials
- 2020
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Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7052 .- 1523-7060. ; 22:21, s. 8387-8391
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Tidskriftsartikel (refereegranskat)abstract
- Here we present a polycyclization of oxotriphenylhexanoates. The polycyclization is governed by electronic effects, and three major synthetic paths have been established leading to stereochemically complex tricyclic frameworks with up to five stereogenic centers. The method is compatible with an array of functional groups, allowing pharmacophoric elements to be introduced post cyclization.
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| 2. |
- Kamlar, Martin, 1981, et al.
(författare)
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Synthesis of cis-Oriented Vicinal Diphenylethylenes through a Lewis Acid-Promoted Annulation of Oxotriphenylhexanoates
- 2021
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 86:13, s. 8660-8671
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Tidskriftsartikel (refereegranskat)abstract
- This study explores the synthesis of cyclic cis-vicinal phenyl ethylenes from oxotriphenylhexanoates. The reaction is a BBr3-promoted cyclization of 1,6-ketoesters (1) to five-membered diketo compounds (2). The synthesis is interesting as it constitutes one of the few examples of modular stereoselective synthesis of structures with a cis-oriented vicinal diphenylethylene. The core structure of 2 can be smoothly derivatized, which makes it a promising synthetic building block for further stereoselective synthetic applications.
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| 3. |
- Zacharias, Savannah C., et al.
(författare)
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Exploring Supramolecular Gels in Flow-Type Chemistry-Design and Preparation of Stationary Phases
- 2021
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Ingår i: Industrial & Engineering Chemistry Research. - : American Chemical Society (ACS). - 0888-5885 .- 1520-5045. ; 60:28, s. 10056-10063
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Tidskriftsartikel (refereegranskat)abstract
- Two major challenges facing chemical synthesis are product isolation and catalyst recovery. One method to overcome these challenges is to perform the synthesis in a flow system with a catalytic stationary phase. However, the polymeric catalytic materials used in flow systems are often laborious to produce. In this study, we investigate a novel supramolecular gel as a catalytic stationary phase material. The gel is based on a modular, easy to synthesize, oxotriphenylhexanoate (OTHO) gelator comprised of a catalytic unit designed to catalyze the Knoevenagel reaction. The catalytic organogel enhances the rate of product formation and can be reused five times. Use of the OTHO to construct catalytic gels is a flexible technique that can be utilized to improve product isolation and reduce wastage of the catalyst.
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