Enantioselective 1,3-dipolar cycloaddition using (z)-amidonitroalkenes as a key step to the access to chiral cis-3,4-diaminopyrrolidines “2279

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SUMMARY

Phosphoramidite (Sa,R,R)-15 in combination with silver perchlorate afforded a high endo-diastereoselection (88:12), good chemical yield (77%), and excellent ee of the endo-9aa cycloadduct. Despite the higher dr (92:8) and identical ee obtained for endo-9aa, the reaction performed at 0 ◦ C occurred in a lower yield than the process run at room temperature. Chiralpak AD-H n-hexane/isopropyl alcohol=90/10, 1.0 mL/min, tRmin: 19.5 min, tRmaj: 25.8 min, 220.5 nm. Chiralpak AD-H n-hexane/isopropyl alcohol=90/10, 1 . . .

 



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