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58149224859
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The steric repulsion effects in Nakatani's cyclization were also observed in the cyclizations of two phenyl butynones. As shown in scheme, the cyclization of 1-[2-(i-butyldimethylsiloxy)-5-methoxyphenyl]butynone 12a showed the six-membered cyclization to give the corresponding chromone 13, while the cyclization of 1-[2-(t-butyldimethylsiloxy)-6- methoxyphenyl]butynone 12b showed the five-membered cyclization to give the corresponding 3(2H)-furanone 14.
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The steric repulsion effects in Nakatani's cyclization were also observed in the cyclizations of two phenyl butynones. As shown in scheme, the cyclization of 1-[2-(i-butyldimethylsiloxy)-5-methoxyphenyl]butynone 12a showed the six-membered cyclization to give the corresponding chromone 13, while the cyclization of 1-[2-(t-butyldimethylsiloxy)-6- methoxyphenyl]butynone 12b showed the five-membered cyclization to give the corresponding 3(2H)-furanone 14.
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14
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0027257609
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Kalinin, V.N.7
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17
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58149245564
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Use of excess Lewis acids, magnesium iodide etherate or aluminium tribromide, caused partial racemization due to a dihydrofuran-ring opening and a following re-cyclization
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Use of excess Lewis acids, magnesium iodide etherate or aluminium tribromide, caused partial racemization due to a dihydrofuran-ring opening and a following re-cyclization.
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