New Chiral Ruthenium Bis(oxazolinyl)pyridine Catalyst. Efficient Asymmetric Cyclopropanation of Olefins with Diazoacetates

Nishiyama, Hisao; Itoh, Yoshiki; Matsui, Hideki; Park, Soon-Bong; Itoh, Kenji

doi:10.1021/ja00084a104

Cited by 410 publications

(163 citation statements)

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“…The use of 0.1 mol % catalyst 31-[G À 2] 8 yielded cyclopropanecarboxylates 74 in 65 ± 98%. The trans/cis ratio was found to be up to 16, which is comparable to those reported for ruthenium-pybox [101] or non-dendritic ruthenium porphyrin catalysts [102] but much higher than those obtained for semi-corrin or bis(oxazoline) copper catalysts.…”

supporting

confidence: 74%

Recent Advances in Asymmetric CC and C‐Heteroatom Bond Forming Reactions using Polymer‐Bound Catalysts

2003

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Dedicated to Professor Dieter Seebach for his achievements in asymmetric catalysis.Abstract: The synthesis of enantiomerically pure compounds is one of the major challenges in organic synthesis. In this review, we present the state of the art in asymmetric catalysis using immobilized chiral ligands and complexes for asymmetric C À C and Cheteroatom bond forming reactions. Chiral catalysts based on dendrimers and soluble polymeric supports are considered. In particular, addition reactions to carbon-carbon double bonds, asymmetric 1,2-addition reactions using, e.g., dialkylzinc reagents, metalcatalyzed substitution reactions and cycloaddition reactions are covered. Specific emphasis is placed on enantioselective epoxidation and aldol reactions. A further aspect is the (hetero) Diels±Alder reaction catalyzed by immobilized ligands.

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confidence: 74%

Recent Advances in Asymmetric CC and C‐Heteroatom Bond Forming Reactions using Polymer‐Bound Catalysts

2003

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“…[7] We eventually found the following optimal procedure: racemic trans-cyclooctene 1 (0.4 mmol, 2 equiv with respect to 2) was added to a solution of [{(p-cymene)RuCl 2 } 2 ] (2) and pybox-ip 3 (1 equiv with respect to 2) in dichloro- :5). Chromatographic separation of the residue through silica gel at 0 8C afforded only complex 4 R in 93 % yield, whereas complex 4 S could not be isolated because of decomposition (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Chiral Bis(dihydrooxazolyl)pyridineruthenium Complexes oftrans-Cyclooctene andtrans-Cycloheptene

Nishiyama¹,

Naitoh²,

Motoyama³

et al. 1999

Chem. Eur. J.

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Asymmetric reaction of an excess of trans-cyclooctene (1) with chiral bis(dihydrooxazolyl)pyridineruthenium (pybox-ip, 3) complex selectively gives the corresponding ruthenium complex 4 R, [RuCl 2 (pybox-ip){(R)-trans-cyclooctene}], and (S)-trans-cyclooctene 2 S. The X-ray crystal structure of complex 4 R shows a C25-C18-C19-C20 dihedral angle of 1258 with a C18ÀC19 bond length of 1.41 . Complex 4 R can also be obtained by UV irradiation of a solution of cis-cyclooctene and [RuCl 2 -(pybox-ip)(C 2 H 4 )] (8) in THF in the presence of a photosensitizer. Even in the absence of the photosensitizer, 4 R is produced by irradiation in the presence of cis-cyclooctene. The photoreaction has been applied to cis-cycloheptene to give a 1:1 mixture of the diastereomeric complexes of [Ru(pybox-ip)-{trans-cycloheptene}].

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“…The reaction using [Ru(p-cymene)Cl 2 ] 2 resulted in only a trace amount of product (Table 1 entry 2). 15 In addition, Cu(I) and Co(II) acetate did not promote the reaction, and starting material was recovered (Table 1, entries 3 and 4). 16 In contrast, Rh 2 (OAc) 4 smoothly catalyzed the reaction to give the cylopropanation adduct in 97% yield with 95:5 diastereoselectivity (Table 1, entry 5).…”

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Catalytic Asymmetric Cyclopropanation with Diazooxindole

Awata

Arai

2012

Synlett

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New Chiral Ruthenium Bis(oxazolinyl)pyridine Catalyst. Efficient Asymmetric Cyclopropanation of Olefins with Diazoacetates

Cited by 410 publications

References 1 publication

Recent Advances in Asymmetric CC and C‐Heteroatom Bond Forming Reactions using Polymer‐Bound Catalysts

Recent Advances in Asymmetric CC and C‐Heteroatom Bond Forming Reactions using Polymer‐Bound Catalysts

Chiral Bis(dihydrooxazolyl)pyridineruthenium Complexes oftrans-Cyclooctene andtrans-Cycloheptene

Catalytic Asymmetric Cyclopropanation with Diazooxindole

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