Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene
نویسندگان
چکیده
منابع مشابه
Stereodivergent, Diels-Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application.
Chiral α,β-unsaturated acylammonium salts are novel dienophiles enabling enantioselective Diels-Alder-lactonization (DAL) organocascades leading to cis- and trans-fused, bicyclic γ- and δ-lactones from readily prepared dienes, commodity acid chlorides, and a chiral isothiourea organocatalyst under mild conditions. We describe extensions of stereodivergent DAL organocascades to other racemic die...
متن کاملAcylammonium Salts as Dienophiles in Diels–Alder/Lactonization Organocascades
α,β-Unsaturated acylammonium salts, generated in situ from commodity acid chlorides and a chiral isothiourea organocatalyst, comprise a new and versatile family of chiral dienophiles for the venerable Diels-Alder (DA) cycloaddition. Their reactivity is unveiled through a highly diastereo- and enantioselective Diels-Alder/lactonization organocascade that generates cis- and trans-fused bicyclic γ...
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Two new surfactant molecules are reported that contain thermally labile Diels-Alder adducts connecting the hydrophilic and hydrophobic sections of each molecule. The two surfactants possess identical hydrophobic dodecyl tail segments but have phenol and carboxylic acid hydrophilic headgroups, respectively. Deprotonation with potassium hydroxide affords the formation of water-soluble surfactants...
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Like molecules of life (e.g., proteins and DNA), many pharmaceutical drugs are also asymmetric (chiral); they are not superimposable on their mirror images. One mirror image form (enantiomer) of a drug can have desirable activity, the other not. Consequently, the development of methods for the selective synthesis of one enantiomer is of great scientific and economic importance. We report here t...
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A highly enantioselective, quinone Diels-Alder reaction catalyzed by chiral samarium and gadolinium pyridyl-bis(oxazoline) (pybox) complexes has been developed. The reaction scope has been extended to include three quinones and five dienes, all of which exclusively provide the expected endo product in excellent yields and enantioselectivities.
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ژورنال
عنوان ژورنال: Organic & Biomolecular Chemistry
سال: 2017
ISSN: 1477-0520,1477-0539
DOI: 10.1039/c6ob02738e