20. Epoxidation of CDX double bonds |
1243 |
Of peracids, MCPBA and (C)-MPCA are used most often. Oxidation is usually carried out in aprotic solvents, mostly in CH2Cl2, CHCl3, or with phase-transfer catalysis. Perfluorinated oxaziridines are prepared in acetonitrile212,213. The acid side-product, m-chlorobenzoic acid, is insoluble in the solvent and the desired oxaziridine may be prepared in good yield. MCPBA, however, is expensive, and large-scale oxidations are sometimes contaminated with bis(m-chlorobenzoyl) peroxide, which complicates product purification206.
Oxone is an inexpensive and stable oxidizing reagent that is commercially available. Replacement of MCPBA by buffered oxone in toluene results in increased yields, a significant reduction of the reaction time and easier purification of the oxaziridine206. In addition, other oxidizing agents were also employed for the epoxidation of imines214 218.
Epoxidation of both aldimines and ketimines is possible. Most oxaziridines formed are stable compounds, especially aldimines containing aromatic substituents, and 2-sulfonyl- and 2-sulfamyl oxaziridines5. Generally, N-sulfonyloxaziridines are isolated as stable crystalline solids. Certain compounds are widely used in synthetic organic chemistry as oxygen-transfer reagents (15 17).
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R = Ph, Bu |
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X = Cl, OMe |
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PhSO2 |
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R = Ph, C6 H4 NO2 |
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SO2 R |
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Biphasic buffered oxidation of sulfonylimines usually suffice for stereoselective synthesis of trans-sulfonyl substituted oxaziridines in excellent yields (equation 41)203.
MCPBA
PhSO2 N CHPh BnEt3 N+Cl−/NaHCO3
O Ph
N C |
(41) |
PhSO2 H
Chiral 2-sulfonyl- and 2-sulfamyloxaziridines were also prepared in different ways4,5. Two examples are given in equations 42 and 43207.
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Me |
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Me |
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oxone |
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(42) |
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N: |
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N: |
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SO2 |
SO2 |
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1244 |
Mihaly´ Bartok´ and Gyula Schneider |
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Me |
Me |
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Me |
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oxone |
(43) |
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SO2 |
O SO2 |
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Both isomeric forms of (C)- and ( )-(camphorylsulfonyl)oxaziridines are available by oxidation of the corresponding sulfonimines with buffered potassium peroxymonosulfate (oxone). Since oxidation can only take place from the endo-face of the CDN double bond due to steric blocking of the exo-face, a single oxaziridine isomer is obtained. The enantiomerically pure sulfonimines can be prepared in three steps in better than 80% yield from inexpensive (C)- and ( )-camphor-10-sulfonic acids. Alternatively they are commercially available200.
The oxidation of imines derived from substituted cyclohexanones occurs predominantly from the equatorial direction. However, the product oxaziridines can undergo subsequent equilibration to favor a more stable conformation which places the bulkier nitrogen substituent in an equatorial conformation (equation 44)219.
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Me N |
Me |
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MCPBA |
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Bn |
44
In another example, the cumulative effect of equatorial attack in prochiral cyclohexanoneimines with diastereoselectivity induced by a chiral nitrogen substituent allowed the synthesis of spirocyclic oxaziridines with a high induction of axial dissymmetry. The major oxaziridine isomer results from both the favored equatorial attack and oxidation anti to the chiral nitrogen substituent (equation 45)204
Me
N Ph
MCPBA or
(+) MPCA
85 %
(Ph)
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Me |
Me |
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Me |
N |
Ph |
Ph N |
O Ph |
N O |
N O Ph |
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+ |
(Ph) |
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(Ph) |
(Ph) |
(Ph) |
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74−85% 12−20% 3−5% 1−3% 45
On epoxidation of imines containing several oxidizable functions, significant selectivity was observed in favor of the formation of oxaziridines (equations 46 48)220 222.
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20. Epoxidation of CDX double bonds |
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1245 |
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But (47) |
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OCOY |
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OCOY |
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The metal-catalyzed oxidation of imines using molecular oxygen as the final oxidant and aldehydes as co-reductants has been studied223. Various transition metal complexes have been tested as catalysts and it is found that cobalt complexes can catalyze the selective oxidation of imines to oxaziridines in good yield (ca 80%) (Scheme 4).
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RCOOH |
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O2 |
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CoIIICl2 |
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RCHO |
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CoIIICl2 |
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CoIIICl2 |
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SCHEME 4
C. Reactions of Oxaziridines
Considering that the present paper does not intend to analyze the chemical reactions of oxaziridines, we refer only to some publications in this field published in recent years. Certain oxaziridines undergo stereoelectronically controlled photochemical rearrangement into lactams (equation 49)204,219.
1246 |
Mihaly´ Bartok´ and Gyula Schneider |
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Me |
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Ph |
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O |
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N |
Ph |
(49) |
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hν
R1 |
R2 |
R1 |
R2 |
Oxaziridines are synthetically useful reagents to transfer an oxygen to a variety of substrates. Within this, chiral oxaziridines5,200,202 attained especially great significance.
The research work of recent years includes predominantly the epoxidation of alkenes9,200, asymmetric hydroxylations209,224 228 and the asymmetric oxidation of sulfides to sulfoxides205,209,229,230. Optical yields of practical significance were obtained (>90%). A detailed review published in 1991231 reports about the versatile use of oxaziridines in the field of the electrophilic amination.
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