Development of bifunctional organocatalysts and application to asymmetric total synthesis of naucleofficine I and II

Yong-Hai Yuan, Xue Han, Fu-Ping Zhu, Jin-Miao Tian, Fu-Min Zhang, Xiao-Ming Zhang, Yong-Qiang Tu (), Shao-Hua Wang and Xiang Guo
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Yong-Hai Yuan: Lanzhou University
Xue Han: Lanzhou University
Fu-Ping Zhu: Lanzhou University
Jin-Miao Tian: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University
Fu-Min Zhang: Lanzhou University
Xiao-Ming Zhang: Lanzhou University
Yong-Qiang Tu: Lanzhou University
Shao-Hua Wang: Lanzhou University
Xiang Guo: Lanzhou University

Nature Communications, 2019, vol. 10, issue 1, 1-7

Abstract: Abstract The proline-type organocatalysts has been efficiently employed to catalyze a wide range of asymmetric transformations; however, there are still many synthetically useful and challenging transformations that remain unachievable in an asymmetric fashion. Herein, a chiral bifunctional organocatalyst with a spirocyclic pyrrolidine backbone-derived containing fluoro-alkyl and aryl sulfonamide functionalities, are designed, prepared, and examined in the asymmetric Mannich/acylation/Wittig reaction sequence of 3,4-dihydro-β-carboline with acetaldehyde, acyl halides, and Wittig reagents. As a result, the spirocyclic pyrrolidine trifluoromethanesulfonamide catalyst can facilitate this versatile sequence as demonstrated by 18 examples displaying excellent enantioselectivity (up to 94% ee), as well as moderate to good yields (up to 54% over 3 steps). As a practical application, the asymmetric total synthesis of naucleofficine I (1a) and II (1b) in ten steps have been accomplished.

Date: 2019
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DOI: 10.1038/s41467-019-11382-8

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