- Catalytic Asymmetric Iodoesterification of Simple Alkenes
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Catalytic asymmetric iodoesterification of simple alkenes was achieved using a dinuclear zinc-3,3′-(R,S,S)-bis(aminoimino)binaphthoxide (di-Zn) complex. For iodoesterification using p-methoxybenzoic acid, the N-iodonaphthalenimide (NIN)-I2 system was effective for producing iodoesters in a highly enantioselective manner. The synthetic utility of chiral iodo-p-methoxybenzoates was also demonstrated. The quartet of metal ionic bond, hydrogen bond, halogen bond, and π-π stacking is harmonized on the single reaction sphere of di-Zn catalyst for enabling the highly enantioselective catalytic asymmetric iodoesterification of simple alkenes for the first time.
- Arai, Takayoshi,Horigane, Kodai,Itoh, Ryosuke,Suzuki, Takumi K.,Yamanaka, Masahiro
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- OPTICALLY ACTIVE AZIDE ESTER AND METHOD FOR PRODUCING THE SAME
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PROBLEM TO BE SOLVED: To provide a novel optically active azide ester and a method for producing the same. SOLUTION: The present invention discloses a series of methods whereby: a zinc binuclear complex catalyst composed of a 3,3'-amino imino binaphthol ligand and a zinc carboxylate is used to produce an optically active iodoester; and from the resultant optically active iodoester and a sodium azide, an optically active azide ester represented by formula (5) is produced (where R1, R3 each denote a hydrogen atom, an alkyl group, an aryl group, halogen atom, an alkoxy group, or a carbonyl group, R2 is a hydrogen atom or an alkyl group). SELECTED DRAWING: None COPYRIGHT: (C)2022,JPOandINPIT
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Paragraph 0017; 0023
(2021/11/02)
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- Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes
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A novel and inexpensive, environmentally friendly method for the preparation of iodine monoacetate is presented using iodine and Oxone in acetic acid/acetic anhydride. The reagent is used in a highly efficient approach for the regio- and diastereoselective iodo-acetoxylation of alkenes and alkynes in a simple one-pot process.
- Hokamp, Tobias,Storm, Alena Therese,Yusubov, Mekhman,Wirth, Thomas
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supporting information
p. 415 - 418
(2017/10/30)
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- Regioselective vicinal functionalization of unactivated alkenes with sulfonium iodate(i) reagents under metal-free conditions
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Metal-free, molecular iodine-free direct 1,2-difunctionalization of unactivated alkenes has been reported. The sulfonium iodate(i) reagent efficiently promoted the intermolecular vicinal iodo-functionalization of a diverse range of olefins in a stereo and regioselective manner. This method enables the divergent and straightforward preparation of synthetically useful functionalities; β-iodocarboxylates, β-iodohydrins, and β-iodoethers in a one-step process. Further interconversion of iodo-functionalized derivatives allows easy access to valuable synthetic intermediates en route to biologically active molecules.
- Rao, Dodla S.,Reddy, Thurpu R.,Babachary, Kalvacherla,Kashyap, Sudhir
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p. 7529 - 7543
(2016/08/16)
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- Synthesis of α-iodoacetates from alkenes by cadmium acetate catalysed Woodward's reaction
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Alkenes on treatment with iodine and cadmium acetate in acetic acid give α-iodoacetates in high yields. The reaction is facile and α-iodoacetates are obtained from both acyclic and cyclic alkenes within 5-30 min.
- Myint, Yi Yi,Pasha
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p. 333 - 335
(2007/10/03)
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- Preparation of α-iodoacetates from alkenes by Co(OAc)2 catalysed Woodward-Prevost reaction
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Woodward-Prevost reaction of alkenes with iodine and cobalt(II) acetate in acetic acid is reported. The reaction is facile and α-iodoacetates are obtained from both acyclic and cyclic alkenes in high yields within 15-55 min.
- Myint, Yi Yi,Pasha
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p. 590 - 592
(2007/10/03)
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