One-pot Synthesis of Chiral cis-Hydrindanes via Diphenylprolinol Silyl Ether Mediated Domino Reaction and Aldol Condensation

Nariyoshi Umekubo; Ryohei Iwata; Yujiro Hayashi

doi:10.1246/cl.200297

One-pot Synthesis of Chiral cis-Hydrindanes via Diphenylprolinol Silyl Ether Mediated Domino Reaction and Aldol Condensation

Nariyoshi Umekubo, Ryohei Iwata, Yujiro Hayashi

SCI - Chemistry

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

7 Citations (Scopus)

Abstract

Substituted chiral hydrindanes were synthesized as single isomers in almost enantiopure forms through a one-pot process that proceeds via the diphenylprolinol silyl ether mediateddomino Michael/Michael reaction of α,β-unsaturated aldehydes and 3-hexene-2,5-dione, and a subsequent intramolecular aldol condensation of the generated cyclopentanone intermediate.

Original language	English
Pages (from-to)	867-869
Number of pages	3
Journal	Chemistry Letters
Volume	49
Issue number	7
DOIs	https://doi.org/10.1246/cl.200297
Publication status	Published - 2020 Jul

Keywords

Domino reaction
Michael reaction
Organocatalyst

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.200297

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title = "One-pot Synthesis of Chiral cis-Hydrindanes via Diphenylprolinol Silyl Ether Mediated Domino Reaction and Aldol Condensation",

abstract = "Substituted chiral hydrindanes were synthesized as single isomers in almost enantiopure forms through a one-pot process that proceeds via the diphenylprolinol silyl ether mediateddomino Michael/Michael reaction of α,β-unsaturated aldehydes and 3-hexene-2,5-dione, and a subsequent intramolecular aldol condensation of the generated cyclopentanone intermediate.",

keywords = "Domino reaction, Michael reaction, Organocatalyst",

author = "Nariyoshi Umekubo and Ryohei Iwata and Yujiro Hayashi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number JP20H04801 in Hybrid Catalysis for Enabling Molecular Synthesis on Demand, and JP19H05630. Publisher Copyright: {\textcopyright} 2020 Chemical Society of Japan. All rights reserved.",

year = "2020",

month = jul,

doi = "10.1246/cl.200297",

language = "English",

volume = "49",

pages = "867--869",

journal = "Chemistry Letters",

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T1 - One-pot Synthesis of Chiral cis-Hydrindanes via Diphenylprolinol Silyl Ether Mediated Domino Reaction and Aldol Condensation

AU - Umekubo, Nariyoshi

AU - Iwata, Ryohei

AU - Hayashi, Yujiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number JP20H04801 in Hybrid Catalysis for Enabling Molecular Synthesis on Demand, and JP19H05630. Publisher Copyright: © 2020 Chemical Society of Japan. All rights reserved.

PY - 2020/7

Y1 - 2020/7

N2 - Substituted chiral hydrindanes were synthesized as single isomers in almost enantiopure forms through a one-pot process that proceeds via the diphenylprolinol silyl ether mediateddomino Michael/Michael reaction of α,β-unsaturated aldehydes and 3-hexene-2,5-dione, and a subsequent intramolecular aldol condensation of the generated cyclopentanone intermediate.

AB - Substituted chiral hydrindanes were synthesized as single isomers in almost enantiopure forms through a one-pot process that proceeds via the diphenylprolinol silyl ether mediateddomino Michael/Michael reaction of α,β-unsaturated aldehydes and 3-hexene-2,5-dione, and a subsequent intramolecular aldol condensation of the generated cyclopentanone intermediate.

KW - Domino reaction

KW - Michael reaction

KW - Organocatalyst

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JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

IS - 7

ER -

One-pot Synthesis of Chiral cis-Hydrindanes via Diphenylprolinol Silyl Ether Mediated Domino Reaction and Aldol Condensation

Abstract

Keywords

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