Pd-Catalyzed Stereoselective Construction of Benzo-Fused Decalines with a Quaternary Carbon

Hideo Setsumasa; Kosuke Imai; Ikumi Kobayashi; Masahisa Nakada

doi:10.1021/acs.orglett.3c02233

Pd-Catalyzed Stereoselective Construction of Benzo-Fused Decalines with a Quaternary Carbon

Hideo Setsumasa, Kosuke Imai, Ikumi Kobayashi, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

The Pd-catalyzed stereoselective construction of decalins with one-carbon units bearing heteroatoms at the ring junction is described. The Pd-catalyzed cyclization of silyl enol ether resulted in exclusive formation of the cis isomer (89%, >100/1 cis/trans). On the contrary, Pd-catalyzed carboiodination and carboborylation (with oxidative workup) provided products in 56% yield (1/>100 cis/trans) and 69% yield (1/11 cis/trans), respectively.

Original language	English
Pages (from-to)	7953-7957
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	44
DOIs	https://doi.org/10.1021/acs.orglett.3c02233
Publication status	Published - 2023 Nov 10

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.3c02233

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abstract = "The Pd-catalyzed stereoselective construction of decalins with one-carbon units bearing heteroatoms at the ring junction is described. The Pd-catalyzed cyclization of silyl enol ether resulted in exclusive formation of the cis isomer (89%, >100/1 cis/trans). On the contrary, Pd-catalyzed carboiodination and carboborylation (with oxidative workup) provided products in 56% yield (1/>100 cis/trans) and 69% yield (1/11 cis/trans), respectively.",

author = "Hideo Setsumasa and Kosuke Imai and Ikumi Kobayashi and Masahisa Nakada",

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AU - Setsumasa, Hideo

AU - Imai, Kosuke

AU - Kobayashi, Ikumi

AU - Nakada, Masahisa

PY - 2023/11/10

Y1 - 2023/11/10

N2 - The Pd-catalyzed stereoselective construction of decalins with one-carbon units bearing heteroatoms at the ring junction is described. The Pd-catalyzed cyclization of silyl enol ether resulted in exclusive formation of the cis isomer (89%, >100/1 cis/trans). On the contrary, Pd-catalyzed carboiodination and carboborylation (with oxidative workup) provided products in 56% yield (1/>100 cis/trans) and 69% yield (1/11 cis/trans), respectively.

AB - The Pd-catalyzed stereoselective construction of decalins with one-carbon units bearing heteroatoms at the ring junction is described. The Pd-catalyzed cyclization of silyl enol ether resulted in exclusive formation of the cis isomer (89%, >100/1 cis/trans). On the contrary, Pd-catalyzed carboiodination and carboborylation (with oxidative workup) provided products in 56% yield (1/>100 cis/trans) and 69% yield (1/11 cis/trans), respectively.

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JO - Organic Letters

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Pd-Catalyzed Stereoselective Construction of Benzo-Fused Decalines with a Quaternary Carbon

Abstract

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