One-pot synthesis of chiral bicyclo[3.3.0]octatrienes using diphenylprolinol silyl ether-mediated ene-type reaction

Hiroaki Gotoh; Hiroshi Ogino; Hayato Ishikawa; Yujiro Hayashi

doi:10.1016/j.tet.2010.03.010

One-pot synthesis of chiral bicyclo[3.3.0]octatrienes using diphenylprolinol silyl ether-mediated ene-type reaction

Hiroaki Gotoh, Hiroshi Ogino, Hayato Ishikawa, Yujiro Hayashi

SCI - Chemistry

Tokyo University of Science

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

18 Citations (Scopus)

Abstract

Chiral bicyclo[3.3.0]octatrienes with excellent enantioselectivity were synthesized from the simple starting materials of α,β-unsaturated aldehyde and cyclopentadiene via one-pot operation, which consisted of a diphenylprolinol silyl ether-mediated ene-type reaction, intramolecular addition reaction of cyclopentadiene moiety with aldehyde and dehydration reaction.

Original language	English
Pages (from-to)	4894-4899
Number of pages	6
Journal	Tetrahedron
Volume	66
Issue number	26
DOIs	https://doi.org/10.1016/j.tet.2010.03.010
Publication status	Published - 2010 Jun 26

Keywords

Asymmetric reaction
ene-Reaction
One-pot reaction
Organocatalyst

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10.1016/j.tet.2010.03.010

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title = "One-pot synthesis of chiral bicyclo[3.3.0]octatrienes using diphenylprolinol silyl ether-mediated ene-type reaction",

abstract = "Chiral bicyclo[3.3.0]octatrienes with excellent enantioselectivity were synthesized from the simple starting materials of α,β-unsaturated aldehyde and cyclopentadiene via one-pot operation, which consisted of a diphenylprolinol silyl ether-mediated ene-type reaction, intramolecular addition reaction of cyclopentadiene moiety with aldehyde and dehydration reaction.",

keywords = "Asymmetric reaction, ene-Reaction, One-pot reaction, Organocatalyst",

author = "Hiroaki Gotoh and Hiroshi Ogino and Hayato Ishikawa and Yujiro Hayashi",

note = "Funding Information: N.W.K. wishes to acknowledge financial support from the Agricultural and Food Research Council. We thank Mr. A. M. Johnston for permission to quote his unpublished data.",

year = "2010",

month = jun,

day = "26",

doi = "10.1016/j.tet.2010.03.010",

language = "English",

volume = "66",

pages = "4894--4899",

journal = "Tetrahedron",

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T1 - One-pot synthesis of chiral bicyclo[3.3.0]octatrienes using diphenylprolinol silyl ether-mediated ene-type reaction

AU - Gotoh, Hiroaki

AU - Ogino, Hiroshi

AU - Ishikawa, Hayato

AU - Hayashi, Yujiro

N1 - Funding Information: N.W.K. wishes to acknowledge financial support from the Agricultural and Food Research Council. We thank Mr. A. M. Johnston for permission to quote his unpublished data.

PY - 2010/6/26

Y1 - 2010/6/26

N2 - Chiral bicyclo[3.3.0]octatrienes with excellent enantioselectivity were synthesized from the simple starting materials of α,β-unsaturated aldehyde and cyclopentadiene via one-pot operation, which consisted of a diphenylprolinol silyl ether-mediated ene-type reaction, intramolecular addition reaction of cyclopentadiene moiety with aldehyde and dehydration reaction.

AB - Chiral bicyclo[3.3.0]octatrienes with excellent enantioselectivity were synthesized from the simple starting materials of α,β-unsaturated aldehyde and cyclopentadiene via one-pot operation, which consisted of a diphenylprolinol silyl ether-mediated ene-type reaction, intramolecular addition reaction of cyclopentadiene moiety with aldehyde and dehydration reaction.

KW - Asymmetric reaction

KW - ene-Reaction

KW - One-pot reaction

KW - Organocatalyst

UR - http://www.scopus.com/inward/record.url?scp=77954244524&partnerID=8YFLogxK

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U2 - 10.1016/j.tet.2010.03.010

DO - 10.1016/j.tet.2010.03.010

M3 - Article

AN - SCOPUS:77954244524

SN - 0040-4020

VL - 66

SP - 4894

EP - 4899

JO - Tetrahedron

JF - Tetrahedron

IS - 26

ER -

One-pot synthesis of chiral bicyclo[3.3.0]octatrienes using diphenylprolinol silyl ether-mediated ene-type reaction

Abstract

Keywords

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