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Applications of Danishefsky’s dienes in asymmetric Oxo-Diels-Alder reactions |
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| Authors: | Afsaneh Taheri kal Koshvandi Majid M Heravi |
| Institution: | Department of Chemistry, Alzahra University, Vanak, Tehran, Iran |
| Abstract: | Applications of Danishefsky’s dienes in catalytic asymmetric hetero-Diels-Alder (AHDA) reactions or specifically, their asymmetric Oxo-Diels-Alder (AOxo-DA) reactions with appropriate dienophiles are highlighted in detail, including the preparation of catalysts with discussion from a mechanistic points of view. Danishefsky’s dienes are effective and useful compounds for the synthesis of optically active six-membered rings such as dihydropyrones, dihydropyridones and dihydropyrans. Due to the broad range of the overall subject, we have limited ourselves, to the recent developments in the utility of Danishefsky’s dienes in the reaction with carbonyl compounds (aldehydes, ketones and 1,2-dicarbonyl compounds) in asymmetric Oxo-Diels-Alder (AOxo-DA) reactions. |
| Keywords: | CAB a stable chiral (acy1oxy)borane TBME EDOT 3 4-ethylenedioxythiophene CAN a chiral Ce(IV) complex from ammonium cerium(IV) nitrate TADDOL α α α′ α′-tetraaryl-1 3-dioxolane-4 5-dimethanols 5-C1-BIPOL 5 5′-dichloro-4 4′ 6 6′-tetramethylbiphenol BINOL binaphthol TBS DPENTf DABNTf TBDPS PMB 4-methoxybenzyl ether TFA trifluoroacetic anhydride PEG poly(ethylene glycol) DMF dimethylformamide titanium isopropoxide TBAT tetrabutylammonium triphenyldifluorosilicate TMSF trimethylenesulfide (?)-DIOP (?)-CHIRAPHOS BNP (1 1′-binaphthyl-2 2′-diylphosphate) TON turnover numbers Phebox 2 6-bis(oxazolinyl)phenyl |
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