Asymmetric imidation of organic selenides into selenimides

Miyake, Yoshihiro; Oda, Masahiko; Oyamada, Arihiro; Takada, Hiroya; Ohe, Kouichi; Uemura, Sakae

doi:10.1016/s0022-328x(00)00488-5

Cited by 26 publications

(9 citation statements)

References 42 publications

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“…Likewise, a direct catalytic sulfimidation of sulfides or 1,3-dithianes with PhINTs using a catalytic amount of copper(I) triflate and a chiral 4,4‘-disubstituted bis(oxazoline) as ligand affords the respective chiral monosulfimides in good yield and with moderate enantioselectivity of up to 40−71% ee. , Under similar conditions, various prochiral selenides react with PhINTs in the presence of CuOTf and the chiral 4,4‘-disubstituted 2,2‘-bis(oxazoline) ligands to give the corresponding chiral selenimides with up to 64% yield and 36% ee. , …”

Section: Imidations At Non-carbon Atomsmentioning

confidence: 99%

Recent Developments in the Chemistry of Polyvalent Iodine Compounds

2002

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Section: Imidations At Non-carbon Atomsmentioning

confidence: 99%

Recent Developments in the Chemistry of Polyvalent Iodine Compounds

2002

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“…Since the excellent chemical and acceptable optical yields were attained, the potential of optical activation leading to chiral organoselenium compound is evident. Uemura et al have already described the catalytic enantioselective imidation of prochiral organic selenides into the corresponding optically active N-tosylselenimides (up to 36% ee), as shown in Equation 35 [37]. The asymmetric catalytic carbenoid addition to chalcogen atoms such as selenium and sulfur appeared in 1995, and then allylic selenium ylides were employed in asymmetric [2,3]-sigmatropic rearrangement [44].…”

Section: Chiral Catalyst-controlled Methodsmentioning

confidence: 99%

“…Uemura et al has already demonstrated the asymmetric induction to several organoselenium compounds to afford chiral organic selenoxides [37]. Very recently, optically active seleninamides were obtained for the first time through …”

Section: Optically Active Selenoxidesmentioning

confidence: 99%

Asymmetric Synthesis of Chiral Organoselenium Compounds

Chengjian¹,

Huang²

2006

COC

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Chiral organoselenium compounds can be attained from three types of asymmetric synthesis. Chiral substratecontrolled methods, chiral auxiliary-controlled methods, and chiral catalyst-controlled methods toward optically active organoselenium derivatives were illustrated. The strategy and classification of methods underlying all asymmetric synthesis therefore involve enantiomerically pure compounds to influence the stereochemical outcome of the reactions. In this review, the advances in asymmetric synthesis of some important classes of chiral organoselenium compounds were described. A. INTRODUCTIONThe asymmetric synthesis of optically active organoselenium compounds constitutes engaging fundamental problems in both scientific research and drug discovery [1]. Over past several years, chiral organoselenium compounds have received a new impetus in the preparations, developments, and asymmetric transformations. The development of stereoselective reactions to form C-Se, Se-Se, Se-O, Sehalogen, Se-N bonds has witnessed the burgeoning levels of diversity, efficiency and applicability [2]. Different chiral selenoorganic functional groups and reagents could be easily synthesized in various means. Optically active diselenides,arylseleno alcohols, -oxo--seleno esters, oxaselenazoles, selenoxides, seleninamides and selenonium ylides were obtained and utilized for some facile transformations, in which these chiral motifs play the critical roles in controlling both the course of the reaction and the stereoselectivity for the specific structural and electronic features [3]. In this review, the recent progress of synthetic methods for some important classes of chiral organoselenium compounds are described. We illustrate three types of asymmetric synthesis according to how the enantiomerically pure compound is used, excluding those processes that involve the derivatization of a reagent without creating any new stereogenic element. The known methods which have been used in asymmetric synthesis of chiral organoselenium compounds are classified into three types:(i) chiral substrate-controlled methods;(ii) chiral auxiliary-controlled methods; (iii) chiral catalyst-controlled methods. B. CHIRAL SUBSTRATE-CONTROLLED METHODSThe chiral substrate-controlled methods may be represented as Equation 1, the influence of an adjacent stereogenic group (X*) involves the formation of a new

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“…135,136 Under similar conditions, prochiral selenides react with PhINTs in the presence of CuOTf and the chiral 4,4'-disubstituted 2,2'-bis(oxazoline) ligands to give the corresponding chiral selenimides with up to 64% yield and 36% ee. 137,138 The reaction of 3,4-di-tert-butylthiophene 42 with PhINTs in the presence of copper(I) or copper(II) catalysts affords a mixture of imide 43 and diimide 44 as principal products (Scheme 17). [139][140][141] The imidation of thiophene 1-oxides 45 under similar conditions gives imides 46 in good yield.…”

Section: Scheme 16mentioning

confidence: 99%

Iodonium imides in organic synthesis

Yoshimura¹,

Yusubov²,

Zhdankin³

2019

Arkivoc

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Iodonium imides (ArINR) represent an important class of hypervalent iodine(III) compounds recently emerging as versatile, efficient and environmentally friendly synthetic reagents with numerous applications in academic and industrial research. Iodonium imides, which are also known as iminoiodanes, are widely used in organic synthesis as common nitrene precursors in the aziridination of alkenes and the amidation reactions of various organic substrates. In the present review, the preparation and structural features of iminoiodanes are discussed, and recent developments in their synthetic applications are summarized.

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Asymmetric imidation of organic selenides into selenimides

Cited by 26 publications

References 42 publications

Recent Developments in the Chemistry of Polyvalent Iodine Compounds

Recent Developments in the Chemistry of Polyvalent Iodine Compounds

Asymmetric Synthesis of Chiral Organoselenium Compounds

Iodonium imides in organic synthesis

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