New chiral diamide ligands: synthesis and application in allylic alkylation

Bateman, Lorraine M.; Breeden, Simon W.; O’Leary, Patrick

doi:10.1016/j.tetasy.2008.01.018

Cited by 21 publications

(19 citation statements)

References 25 publications

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“…1). The chemical structures of the isolated compounds were unambiguously elucidated to be (R)-5-hydroxypyrrolidin-2-one (1,15), methyl (R)-pyroglutamate (2,16), loliolide (3,17), 3-benzofurancarboxalde hyde (4,18), odisolane (5,19), and indole (6,20) by comparing their NMR spectroscopic values and physical properties with previously reported literature data.…”

Section: Resultsmentioning

confidence: 86%

Identification of bioactive heterocyclic compounds from mulberry and their protective effect against streptozotocin-induced apoptosis in INS-1 cells

Song

Lee

et al. 2018

Mol Med Report

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A phytochemical investigation of the MeOH extracts from mulberries (the fruit of Morus alba L.) led to the identification of six heterocyclic compounds (1‑6). These compounds were screened to detect whether they protected pancreatic INS‑1 cells from streptozotocin (STZ)‑induced cytotoxicity. Compound 3 was the most effective at preventing STZ‑induced cytotoxicity and the production of reactive oxygen species (ROS) in INS‑1 cells. In addition, compound 3 effectively prevented apoptosis induced by STZ in INS‑1 cells. Compound 3 also prevented STZ‑mediated cleavage of caspase‑8, caspase‑3 and poly (ADP‑ribose) polymerase and increased the expression of B‑cell lymphoma‑2 (Bcl‑2), an anti‑apoptotic Bcl‑2 family protein. In conclusion, the results of the present study indicate that compound 3 extracted from the fruit of M. alba was highly effective in preventing type 1 diabetes mellitus and may be a novel treatment option.

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Section: Resultsmentioning

confidence: 86%

Identification of bioactive heterocyclic compounds from mulberry and their protective effect against streptozotocin-induced apoptosis in INS-1 cells

Song

Lee

et al. 2018

Mol Med Report

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“…Selective reduction of the ester to the primary alcohol followed by mesylation and displacement with sodium azide afforded 23 , a sequence previously reported by Bateman et al [29] In an analogy to the protocol described by Knight and Leeper [21] and ourselves, [30] 23 was methylated with Meerwein’s salt to give neutral imidate 24 in 85% yield. Condensation with N -mesitylhydrazine hydrochloride afforded 26 , which was further used without purification to generate N -mesityl triazolium chloride 27 .…”

Section: Resultsmentioning

confidence: 95%

Late‐Stage Diversification of Chiral N‐Heterocyclic‐Carbene Precatalysts for Enantioselective Homoenolate Additions

Zheng¹,

Gondo²,

Bode³

2010

Chemistry An Asian Journal

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A library of chiral triazolium salts has been prepared by late-state diversification of a triazolium amine salt. By utilizing a primary amine as a functional handle, a single triazolium salt can be transformed into a variety of chiral N-heterocyclic carbene precatalysts. This approach makes the preparation of chiral N-heterocyclic carbenes possible by a single-step modification of a triazolium salt, rather than the usual need for multistep organic synthesis and challenging heterocycle formation for each member of a catalyst library. We have screened these catalysts for control of diastereo- and enantioselectivity in a γ-lactam-forming reaction between α,β-unsaturated aldehydes and cyclic ketimines.

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“…A ligand with a side chain containing an amide and a lactam (L110) has been developed by O'Leary [139]. Very good ee's up to 93% were recorded when used in standard AAA, but information is lacking about the mode of coordination as such compounds may bind through an oxygen instead of the nitrogen of the amide.…”

Section: Pyridine-based Ligandsmentioning

confidence: 99%

Palladium-Catalyzed Enantioselective Allylic Substitution

Milhau

Guiry

2011

Topics in Organometallic Chemistry

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Palladium-catalyzed allylic substitution is one of the main reactions for testing new chiral ligands. The most relevant examples from the work published in the period 2007 to mid-2010 are reviewed. The vast majority of the work published within this timeframe relies upon the application of chiral ligands for asymmetric induction. The recent advances in the development and applications of new chiral P-P, P-N, P-O, P-S, N-N, N-S, S-S, and NHC ligands are covered and are the main focus of this chapter. Other aspects of enantioselective palladium allylic alkylations are discussed in the subsequent sections, for example, heterogeneous catalysis, the use of chiral salt additives, and recent applications in kinetic resolution.

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New chiral diamide ligands: synthesis and application in allylic alkylation

Cited by 21 publications

References 25 publications

Identification of bioactive heterocyclic compounds from mulberry and their protective effect against streptozotocin-induced apoptosis in INS-1 cells

Identification of bioactive heterocyclic compounds from mulberry and their protective effect against streptozotocin-induced apoptosis in INS-1 cells

Late‐Stage Diversification of Chiral N‐Heterocyclic‐Carbene Precatalysts for Enantioselective Homoenolate Additions

Palladium-Catalyzed Enantioselective Allylic Substitution

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