光学活性希土類錯体を用いる電子豊富ジエンの触媒的不斉Diels-Alder反応の開発
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概要
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Danishefsky diene (1-methoxy-3-trialkylsiloxy-1,3-butadiene) is known as a reactive and useful substrate for Diels-Alder reaction to give highly functionalized cyclohexenes. However, the diene is so unstable under acidic conditions that applicable Lewis acid to activate dienophile is quite limited. We developed Yb(OTf)3/BINAMIDE or BINUREA/DBU catalyst, which realized the first example of catalytic asymmetric Diels-Alder reaction of Danishefsky diene and electron-deficient olefins. The Diels-Alder reaction of several types of dienophiles with Danishefsky diene was efficiently facilitated by the catalyst to give exclusively exo adducts. The Diels-Alder adduct can be transferred to various synthetic intermediates. Apparent (+)-non-linear effects between asymmetric induction and the enantiomeric composition of BINAMIDE may suggest the possible formation of a reservoir of non-reactive aggregates. A structure of ytterbium salt was discussed.
- 社団法人 有機合成化学協会の論文
社団法人 有機合成化学協会 | 論文
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