Asymmetric synthesis of multisubstituted dihydrobenzofurans by intramolecular conjugate addition of short-lived C-O axially chiral enolates

Keisuke Tomohara; Koji Kasamatsu; Tomoyuki Yoshimura; Takumi Furuta; Takeo Kawabata

doi:10.1248/cpb.c16-00272

Asymmetric synthesis of multisubstituted dihydrobenzofurans by intramolecular conjugate addition of short-lived C-O axially chiral enolates

Keisuke Tomohara, Koji Kasamatsu, Tomoyuki Yoshimura, Takumi Furuta, Takeo Kawabata

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

9 Citations (Scopus)

Abstract

Enantioselective intramolecular conjugate addition reactions of short-lived C-O axially chiral enolates have been developed. The reactions proceeded with inversion of the configuration and provided dihydrobenzofurans with contiguous tetra- and trisubstituted carbon centers in up to 96% enantiomeric excess (ee).

Original language	English
Pages (from-to)	899-906
Number of pages	8
Journal	Chemical and Pharmaceutical Bulletin
Volume	64
Issue number	7
DOIs	https://doi.org/10.1248/cpb.c16-00272
Publication status	Published - 2016
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)
Drug Discovery

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title = "Asymmetric synthesis of multisubstituted dihydrobenzofurans by intramolecular conjugate addition of short-lived C-O axially chiral enolates",

abstract = "Enantioselective intramolecular conjugate addition reactions of short-lived C-O axially chiral enolates have been developed. The reactions proceeded with inversion of the configuration and provided dihydrobenzofurans with contiguous tetra- and trisubstituted carbon centers in up to 96% enantiomeric excess (ee).",

author = "Keisuke Tomohara and Koji Kasamatsu and Tomoyuki Yoshimura and Takumi Furuta and Takeo Kawabata",

note = "Funding Information: This work was also supported by a Grant-in-Aid for JSPS Fellows to K.T. and K.K. Publisher Copyright: {\textcopyright} 2016 The Pharmaceutical Society of Japan.",

year = "2016",

doi = "10.1248/cpb.c16-00272",

language = "English",

volume = "64",

pages = "899--906",

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publisher = "The Pharmaceutical Society of Japan",

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T1 - Asymmetric synthesis of multisubstituted dihydrobenzofurans by intramolecular conjugate addition of short-lived C-O axially chiral enolates

AU - Tomohara, Keisuke

AU - Kasamatsu, Koji

AU - Yoshimura, Tomoyuki

AU - Furuta, Takumi

AU - Kawabata, Takeo

PY - 2016

Y1 - 2016

N2 - Enantioselective intramolecular conjugate addition reactions of short-lived C-O axially chiral enolates have been developed. The reactions proceeded with inversion of the configuration and provided dihydrobenzofurans with contiguous tetra- and trisubstituted carbon centers in up to 96% enantiomeric excess (ee).

AB - Enantioselective intramolecular conjugate addition reactions of short-lived C-O axially chiral enolates have been developed. The reactions proceeded with inversion of the configuration and provided dihydrobenzofurans with contiguous tetra- and trisubstituted carbon centers in up to 96% enantiomeric excess (ee).

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Asymmetric synthesis of multisubstituted dihydrobenzofurans by intramolecular conjugate addition of short-lived C-O axially chiral enolates

Abstract

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