Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant

Hirokazu Tsukamoto; Ayumu Kawase; Takayuki Doi

doi:10.1039/c5cc02176f

Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant

Hirokazu Tsukamoto, Ayumu Kawase, Takayuki Doi

PHA - Molecular Pharmaceutical Science

Tohoku University

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

17 Citations (Scopus)

Abstract

Palladium/chiral diphosphine-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a terminal reductant affords cis-disubstituted pyrrolidine, tetrahydrofuran, and spiro carbocycle in high enantioselectivity. The formate does not cause allylpalladium reduction under the catalysis. The highly stereoselective cyclization would proceed through a cationic η¹-allylpalladium ligated by diphosphine.

Original language	English
Pages (from-to)	8027-8030
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	38
DOIs	https://doi.org/10.1039/c5cc02176f
Publication status	Published - 2015 May 11

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abstract = "Palladium/chiral diphosphine-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a terminal reductant affords cis-disubstituted pyrrolidine, tetrahydrofuran, and spiro carbocycle in high enantioselectivity. The formate does not cause allylpalladium reduction under the catalysis. The highly stereoselective cyclization would proceed through a cationic η1-allylpalladium ligated by diphosphine.",

author = "Hirokazu Tsukamoto and Ayumu Kawase and Takayuki Doi",

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AU - Tsukamoto, Hirokazu

AU - Kawase, Ayumu

AU - Doi, Takayuki

PY - 2015/5/11

Y1 - 2015/5/11

N2 - Palladium/chiral diphosphine-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a terminal reductant affords cis-disubstituted pyrrolidine, tetrahydrofuran, and spiro carbocycle in high enantioselectivity. The formate does not cause allylpalladium reduction under the catalysis. The highly stereoselective cyclization would proceed through a cationic η1-allylpalladium ligated by diphosphine.

AB - Palladium/chiral diphosphine-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a terminal reductant affords cis-disubstituted pyrrolidine, tetrahydrofuran, and spiro carbocycle in high enantioselectivity. The formate does not cause allylpalladium reduction under the catalysis. The highly stereoselective cyclization would proceed through a cationic η1-allylpalladium ligated by diphosphine.

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JO - Chemical Communications

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ER -

Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant

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