科研之友
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摘要
1,3-Dipolar cycloaddition reaction of a carbohydrate-derived exocyclic olefin with in situ generated non-stabilized azomethine ylides, formed by the reaction of sarcosine (a secondary a-amino acid) with isatins, acenaphthenedione and cycloalkanones in refluxing toluene afforded bispiropyrrolidine derivatives in 78-92% yield, when DIPEA was used as a base. However, using Et3N/DBU, the reaction of the olefin precursor with azomethine ylide (derived from the condensation of cyclopentanone and sarcosine) furnished the product in 51-53% yield. On the other hand, in the absence of a base the yield of the cycloaddition product was dramatically decreased to 10-22%.
- 出版日期2013-7-17
