Enantio- and Stereoselective Construction of Atisane Scaffold via Organocatalytic Intramolecular Michael Reaction and Diels-Alder Reaction

Hiroko Sekita; Kyohei Adachi; Ippei Kobayashi; Yusuke Sato; Masahisa Nakada

doi:10.1021/acs.orglett.7b00918

Enantio- and Stereoselective Construction of Atisane Scaffold via Organocatalytic Intramolecular Michael Reaction and Diels-Alder Reaction

Hiroko Sekita, Kyohei Adachi, Ippei Kobayashi, Yusuke Sato, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

6 Citations (Scopus)

Abstract

An enantio- and stereoselective construction of the atisane scaffold via organocatalytic intramolecular Michael reaction and Diels-Alder reaction is described. The organocatalytic intramolecular Michael reaction has been found to stereoselectively generate a trans-stereodiad comprising an all-carbon quaternary and a tertiary stereogenic centers. Use of the chiral secondary amine bearing thiourea with benzoic acid as additive is the key to obtaining the desired product with excellent ee in synthetically acceptable yield. The prepared chiral building block has been successfully converted to the compound including the atisane scaffold via the highly stereoselective intramolecular Diels-Alder reaction.

Original language	English
Pages (from-to)	2390-2393
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.7b00918
Publication status	Published - 2017 May 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Enantio- and Stereoselective Construction of Atisane Scaffold via Organocatalytic Intramolecular Michael Reaction and Diels-Alder Reaction",

abstract = "An enantio- and stereoselective construction of the atisane scaffold via organocatalytic intramolecular Michael reaction and Diels-Alder reaction is described. The organocatalytic intramolecular Michael reaction has been found to stereoselectively generate a trans-stereodiad comprising an all-carbon quaternary and a tertiary stereogenic centers. Use of the chiral secondary amine bearing thiourea with benzoic acid as additive is the key to obtaining the desired product with excellent ee in synthetically acceptable yield. The prepared chiral building block has been successfully converted to the compound including the atisane scaffold via the highly stereoselective intramolecular Diels-Alder reaction.",

author = "Hiroko Sekita and Kyohei Adachi and Ippei Kobayashi and Yusuke Sato and Masahisa Nakada",

note = "Funding Information: We acknowledge support by the Materials Characterization Central Laboratory, Waseda University, for characterization of new compounds. This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas 2707 Middle molecular strategy from MEXT and a Waseda University Grant for Special Research Projects. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b00918",

language = "English",

volume = "19",

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journal = "Organic Letters",

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T1 - Enantio- and Stereoselective Construction of Atisane Scaffold via Organocatalytic Intramolecular Michael Reaction and Diels-Alder Reaction

AU - Sekita, Hiroko

AU - Adachi, Kyohei

AU - Kobayashi, Ippei

AU - Sato, Yusuke

AU - Nakada, Masahisa

N1 - Funding Information: We acknowledge support by the Materials Characterization Central Laboratory, Waseda University, for characterization of new compounds. This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas 2707 Middle molecular strategy from MEXT and a Waseda University Grant for Special Research Projects. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/5/5

Y1 - 2017/5/5

N2 - An enantio- and stereoselective construction of the atisane scaffold via organocatalytic intramolecular Michael reaction and Diels-Alder reaction is described. The organocatalytic intramolecular Michael reaction has been found to stereoselectively generate a trans-stereodiad comprising an all-carbon quaternary and a tertiary stereogenic centers. Use of the chiral secondary amine bearing thiourea with benzoic acid as additive is the key to obtaining the desired product with excellent ee in synthetically acceptable yield. The prepared chiral building block has been successfully converted to the compound including the atisane scaffold via the highly stereoselective intramolecular Diels-Alder reaction.

AB - An enantio- and stereoselective construction of the atisane scaffold via organocatalytic intramolecular Michael reaction and Diels-Alder reaction is described. The organocatalytic intramolecular Michael reaction has been found to stereoselectively generate a trans-stereodiad comprising an all-carbon quaternary and a tertiary stereogenic centers. Use of the chiral secondary amine bearing thiourea with benzoic acid as additive is the key to obtaining the desired product with excellent ee in synthetically acceptable yield. The prepared chiral building block has been successfully converted to the compound including the atisane scaffold via the highly stereoselective intramolecular Diels-Alder reaction.

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JF - Organic Letters

IS - 9

ER -

Enantio- and Stereoselective Construction of Atisane Scaffold via Organocatalytic Intramolecular Michael Reaction and Diels-Alder Reaction

Abstract

ASJC Scopus subject areas

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