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Volumn 50, Issue 15, 1994, Pages 4311-4322

Rational design of Mn-Salen epoxidation catalysts: Preliminary results

(5) Hosoya, Naoki a Hatayama, Akira a Irie, Ryo a Sasaki, Hidehiko a Katsuki, Tsutomu a

a KYUSHU UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; METAL COMPLEX; SALICYLALDEHYDE DERIVATIVE; SALICYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

CATALYSIS; CONFERENCE PAPER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0028356107 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4020(01)89368-6 Document Type: Article

Times cited : (101)

References (27)

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9
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- Donor Ligand Effect in Asymmetric Epoxidation of Unfunctionalized Olefins with Chiral Salen Complexes
- (1991) Synlett , vol.2 , pp. 265
- Irie¹ Ito² Katsuki³

10
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- Irie¹ Noda² Ito³ Matsumoto⁴ Katsuki⁵

11
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- (1992) Synlett , vol.407
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12
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- Jacobsen et al. independently reported salen-catalyzed asymmetric epoxidation of simple olefins:
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- Zhang¹ Loebach² Wilson³ Jacobsen⁴

13
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- Jacobsen¹ Zhang² Guller³

14
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- Jacobsen¹ Zhang² Muci³ Ecker⁴ Deng⁵

15
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- Lee¹ Jacobsen²

16
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- Lee¹ Muci² Jacobsen³

17
- 0000194024
- Enantioselective Epoxidation of Unfunctionalized Olefins with Molecular Oxygen and Aldehyde Catalyzed by Optically Active Manganese(III) Complexes.
- Mukaiyama et al. recently reported salen-catalyzed asymmetric epoxidation using molecular oxygen as a terminal oxidant:
- (1992) Chemistry Letters , pp. 2231
- Yamada¹ Imagawa² Nagata³ Mukaiyama⁴

18
- 84989550908
- Asymmetric Epoxidation with Optically Active (Salen)manganese(III) Complexes: From Which Direction Does the Olefin Approach the Metal-Oxo Bond?
- (1993) Synlett , pp. 641
- Hosoya¹ Hatayama² Yanai³ Fujii⁴ Irie⁵ Katsuki⁶

19
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- Construction of New Optically Active (Salen)manganese(III) Complexes and Their Application to Asymmetric Epoxidation of Styrene Derivatives
- Preliminary results have been partly communicated:
- (1993) Synlett , pp. 261
- Hosoya¹ Irie² Katsuki³

20
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- Catalytic Asymmetric Epoxidation with (Salen)manganese(III) Complex Bearing Binaphthyl Groups of Axial Chirality
- (1993) Synlett , pp. 300
- Sasaki¹ Irie² Katsuki³

21
- 84921165191
- The flexibility of binaphthyl-type structure has already been discussed by Noyori:
- (1982) Kagaku Zoukan , vol.97 , pp. 57
- Noyori¹

22
- 84921165190
- The complex bearing (1R,2R)-cyclohexanediamine as ethylenediamine part showed poor asymmetric induction of 18.6% ee.

23
- 84921165189
- (Salen)manganese(III) complex bearing only cyclohexanediamine as a chiral source, has already been reported to be a good catalyst for the epoxidation of cis-olefins. However, no epoxidation of trans-olefins using the complex has been reported (reference 6c).

24
- 84921165188
- Although we have no certain information about the conformation of C3- and C3′-substituents, inspection of 1 and 8 with CPK model suggests that the conformation wherein aryl groups are directed away from the metal center is preferential. Accordingly, the change from phenyl group (1) to 4-t-butylphenyl group (8) is considered to give almost no influence on enantioselectivity.

25
- 84921165187
- Sasaki, H.; Irie, R.; Katsuki, T. to be published elsewhere.

26
- 84921165186
- Complex 10b was synthesized in a similar manner to that described for 10a.

27
- 84921165185
- 5c, was converted into acid (S)-17 by the sequence: i) FeCl3, t-butyl chloride, ii) NaOH. Chiroptical comparison of (S)-17 and the acid 17 obtained by the resolution with (−)-brucine showed the configuration of the acid 17 to be R.

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