Asymmetric [3 + 2] Cycloaddition of 3‑Amino
Oxindole-Based Azomethine Ylides and α,β-Enones with Divergent
Diastereocontrol on the Spiro[pyrrolidine-oxindoles]
Posted on 2017-03-27 - 20:31
A general and practical
organocatalytic asymmetric 1,3-dipolar
cycloaddition of 3-amino oxindole-based azomethine ylides and α,β-enones
has been developed. This reaction delivered spiro[pyrrolidine-2,3′-oxindole]
products in high yields with excellent regio- and enantioselectivities
(up to 99% yield, >20:1 rr, 99% ee). In addition,
an array of spiro[dihydropyrrole-2,3′-oxindoles] were readily
accessed by oxidative dehydrogenation. Notably, the inversion of the
diastereoselectivity of the spiro[pyrrolidine-oxindole] product could
be easily achieved through a facile oxidation–reduction process.
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Zhu, Guodong; Wei, Qian; Chen, Hongbo; Zhang, Yanpeng; Shen, Wen; Qu, Jingping; et al. (2017). Asymmetric [3 + 2] Cycloaddition of 3‑Amino
Oxindole-Based Azomethine Ylides and α,β-Enones with Divergent
Diastereocontrol on the Spiro[pyrrolidine-oxindoles]. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b00625
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AUTHORS (7)
GZ
Guodong Zhu
QW
Qian Wei
HC
Hongbo Chen
YZ
Yanpeng Zhang
WS
Wen Shen
JQ
Jingping Qu
BW
Baomin Wang