Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center

Shinobu Takizawa; Kenta Kishi; Yasushi Yoshida; Steffen Mader; Fernando Arteaga Arteaga; Shoukou Lee; Manabu Hoshino; Magnus Rueping; Makoto Fujita; Hiroaki Sasai

doi:10.1002/anie.201508022

Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center

Shinobu Takizawa, Kenta Kishi, Yasushi Yoshida, Steffen Mader, Fernando Arteaga Arteaga, Shoukou Lee, Manabu Hoshino, Magnus Rueping, Makoto Fujita, Hiroaki Sasai^*

^*Corresponding author for this work

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

99 Scopus citations

Abstract

An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy-Michael and Rauhut-Currier reactions, produced highly functionalized tetrahydrobenzofuranones, bearing a chiral tetrasubstituted stereogenic center, in up to 96 % ee. Domino effect: An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence involving oxy-Michael and Rauhut-Currier reactions produced highly functionalized tetrahydrobenzofuranones bearing a chiral tetrasubstituted stereogenic center in up to 96 % ee.

Original language	English (US)
Pages (from-to)	15511-15515
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	51
DOIs	https://doi.org/10.1002/anie.201508022
State	Published - Dec 14 2015
Externally published	Yes

Keywords

allenes
annulations
organocatalysis
phosphines
umpolung

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201508022

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Takizawa, S., Kishi, K., Yoshida, Y., Mader, S., Arteaga, F. A., Lee, S., Hoshino, M., Rueping, M., Fujita, M., & Sasai, H. (2015). Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center. Angewandte Chemie - International Edition, 54(51), 15511-15515. https://doi.org/10.1002/anie.201508022

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abstract = "An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy-Michael and Rauhut-Currier reactions, produced highly functionalized tetrahydrobenzofuranones, bearing a chiral tetrasubstituted stereogenic center, in up to 96 % ee. Domino effect: An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence involving oxy-Michael and Rauhut-Currier reactions produced highly functionalized tetrahydrobenzofuranones bearing a chiral tetrasubstituted stereogenic center in up to 96 % ee.",

keywords = "allenes, annulations, organocatalysis, phosphines, umpolung",

author = "Shinobu Takizawa and Kenta Kishi and Yasushi Yoshida and Steffen Mader and Arteaga, {Fernando Arteaga} and Shoukou Lee and Manabu Hoshino and Magnus Rueping and Makoto Fujita and Hiroaki Sasai",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

month = dec,

day = "14",

doi = "10.1002/anie.201508022",

language = "English (US)",

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Takizawa, S, Kishi, K, Yoshida, Y, Mader, S, Arteaga, FA, Lee, S, Hoshino, M, Rueping, M, Fujita, M & Sasai, H 2015, 'Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center', Angewandte Chemie - International Edition, vol. 54, no. 51, pp. 15511-15515. https://doi.org/10.1002/anie.201508022

Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center. / Takizawa, Shinobu; Kishi, Kenta; Yoshida, Yasushi et al.
In: Angewandte Chemie - International Edition, Vol. 54, No. 51, 14.12.2015, p. 15511-15515.

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

TY - JOUR

T1 - Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters

T2 - Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center

AU - Takizawa, Shinobu

AU - Kishi, Kenta

AU - Yoshida, Yasushi

AU - Mader, Steffen

AU - Arteaga, Fernando Arteaga

AU - Lee, Shoukou

AU - Hoshino, Manabu

AU - Rueping, Magnus

AU - Fujita, Makoto

AU - Sasai, Hiroaki

PY - 2015/12/14

Y1 - 2015/12/14

N2 - An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy-Michael and Rauhut-Currier reactions, produced highly functionalized tetrahydrobenzofuranones, bearing a chiral tetrasubstituted stereogenic center, in up to 96 % ee. Domino effect: An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence involving oxy-Michael and Rauhut-Currier reactions produced highly functionalized tetrahydrobenzofuranones bearing a chiral tetrasubstituted stereogenic center in up to 96 % ee.

AB - An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy-Michael and Rauhut-Currier reactions, produced highly functionalized tetrahydrobenzofuranones, bearing a chiral tetrasubstituted stereogenic center, in up to 96 % ee. Domino effect: An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence involving oxy-Michael and Rauhut-Currier reactions produced highly functionalized tetrahydrobenzofuranones bearing a chiral tetrasubstituted stereogenic center in up to 96 % ee.

KW - allenes

KW - annulations

KW - organocatalysis

KW - phosphines

KW - umpolung

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M3 - Article

C2 - 26537173

AN - SCOPUS:84955193973

SN - 1433-7851

VL - 54

SP - 15511

EP - 15515

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 51

ER -

Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center

Abstract

Keywords

ASJC Scopus subject areas

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