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5-steroids by the sterically unhindered dioxiranes, the steric interactions in both β-TS and α-TS appear to be more or less the same; this results in low selectivities. See ref. [14b]
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5-steroids by the sterically unhindered dioxiranes, the steric interactions in both β-TS and α-TS appear to be more or less the same; this results in low selectivities. See ref. [14b].
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Epoxidation of substrates 6-11 with mCPBA was also carried out for comparison (see Table 1); this gave α-epoxides as the major products
-
Epoxidation of substrates 6-11 with mCPBA was also carried out for comparison (see Table 1); this gave α-epoxides as the major products.
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57
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0347553900
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5-unsaturated steroids is not compatible with some metal-based oxidants in the epoxidation reactions. See references [9c,f]
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5-unsaturated steroids is not compatible with some metal-based oxidants in the epoxidation reactions. See references [9c,f].
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58
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0033525675
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This is in agreement with our previous observation on diastereoselectivities exhibited by ketones 1-5 for epoxidation of cyclohexenes with allylic substituents. See: D. Yang, G.-S. Jiao, Y-C. Yip, M.-K. Wong, J. Org. Chem. 1999, 64, 1635.
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0346922810
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Since the 3α-substituents of steroids 13-21 are bulky enough to block the approach of dioxiranes from the α-face, the ratio of β/α epoxides is generally high (43:1 to > 99:1)
-
Since the 3α-substituents of steroids 13-21 are bulky enough to block the approach of dioxiranes from the α-face, the ratio of β/α epoxides is generally high (43:1 to > 99:1).
-
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60
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0346922809
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For example, a multi-gram scale (10 mmol) epoxidation of substrate 19 catalyzed by ketone 3 (5 mol %) provided almost exclusively a single β-epoxide (β/α-epoxide ratio > 99:1) in 88% yield
-
For example, a multi-gram scale (10 mmol) epoxidation of substrate 19 catalyzed by ketone 3 (5 mol %) provided almost exclusively a single β-epoxide (β/α-epoxide ratio > 99:1) in 88% yield.
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