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Cycloisomerization/(2+1) Annulation of Enyne-Amide With α-Bromomalonate: A Novel and Selective Access to Oxa/Aza-Spiro[2.4]heptane Derivatives

delete2026-06-17
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PRE
AI
Y
Yujiao Sun
Y
Yongli Li
H
Hui Mao
H
Hongyan Xie *
X
Xin Lv *
L
Liejin Zhou *
DOI：10.1002/ajoc.70471delete
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Abstract

Abstract

En 中文
Oxa- and aza-spiro[2.4]heptane frameworks are privileged scaffolds in bioactive molecules. Herein, we report a catalyst-controlled divergent synthesis of these spirocycles from readily accessible enyne-amides and α-bromomalonates. Under Au(I) catalysis, cycloisomerization generates a furan-fused azadiene intermediate, which undergoes base-promoted (2+1) annulation to afford 5-oxa-spiro[2.4]heptanes with excellent diastereoselectivity (>20:1). In contrast, Pd(II) catalysis triggers an intramolecular hydroamination to form a pyrrole-fused oxodiene, followed by (2+1) annulation to deliver 5-aza-spiro[2.4]heptanes. This protocol enables selective assembly of diverse spirocyclic products under mild conditions, providing good to excellent yields with high diastereoselectivity.
Keywords:
aza-spiro[2.4]heptane
cyclopropanation
domino annulation
enyne-amide
oxa-spiro[2.4]heptane

Journal

Asian Journal of Organic Chemistry cover
Asian Journal of Organic Chemistry
IF:
2.7
Papers:
938
Citations:
6.5K

Organization

Z
zhejiang normal university
Scholars:
2.4K
Papers: 919
Citations: 0
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