Acid-catalyzed intramolecular [2+2] Cycloaddition of ene-allenones: Facile access to bicyclo[n.2.0] frameworks

Jun Feng Zhao; Teck Peng Loh

doi:10.1002/anie.200902471

Acid-catalyzed intramolecular [2+2] Cycloaddition of ene-allenones: Facile access to bicyclo[n.2.0] frameworks

Jun Feng Zhao, Teck Peng Loh

Nanyang Technological University

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

47 Scopus citations

Abstract

Two plus two equals a bicycle: A highly efficient acidcatalyzed intramolecular [2+2] cycloaddition of eneallenones affords strained bicyclo[n.2.0] frameworks, which contain vicinal all-carbon quaternary and tertiary centers (see scheme; Tf: trifluoromethanesulfonyl), under mild conditions with excellent yields and chemo-, regio-, and diastereoselectivities.

Original language	English
Pages (from-to)	7232-7235
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	39
DOIs	https://doi.org/10.1002/anie.200902471
State	Published - 14 Sep 2009
Externally published	Yes

Keywords

Acid catalysis
Cycloaddition
Cyclobutanes
Multiple bonds
Used-ring systems

Access to Document

10.1002/anie.200902471

Cite this

@article{58cd851095704475a6efec7ae4aa55a0,

title = "Acid-catalyzed intramolecular [2+2] Cycloaddition of ene-allenones: Facile access to bicyclo[n.2.0] frameworks",

abstract = "Two plus two equals a bicycle: A highly efficient acidcatalyzed intramolecular [2+2] cycloaddition of eneallenones affords strained bicyclo[n.2.0] frameworks, which contain vicinal all-carbon quaternary and tertiary centers (see scheme; Tf: trifluoromethanesulfonyl), under mild conditions with excellent yields and chemo-, regio-, and diastereoselectivities.",

keywords = "Acid catalysis, Cycloaddition, Cyclobutanes, Multiple bonds, Used-ring systems",

author = "Zhao, {Jun Feng} and Loh, {Teck Peng}",

year = "2009",

month = sep,

day = "14",

doi = "10.1002/anie.200902471",

language = "英语",

volume = "48",

pages = "7232--7235",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "39",

}

TY - JOUR

T1 - Acid-catalyzed intramolecular [2+2] Cycloaddition of ene-allenones

T2 - Facile access to bicyclo[n.2.0] frameworks

AU - Zhao, Jun Feng

AU - Loh, Teck Peng

PY - 2009/9/14

Y1 - 2009/9/14

N2 - Two plus two equals a bicycle: A highly efficient acidcatalyzed intramolecular [2+2] cycloaddition of eneallenones affords strained bicyclo[n.2.0] frameworks, which contain vicinal all-carbon quaternary and tertiary centers (see scheme; Tf: trifluoromethanesulfonyl), under mild conditions with excellent yields and chemo-, regio-, and diastereoselectivities.

AB - Two plus two equals a bicycle: A highly efficient acidcatalyzed intramolecular [2+2] cycloaddition of eneallenones affords strained bicyclo[n.2.0] frameworks, which contain vicinal all-carbon quaternary and tertiary centers (see scheme; Tf: trifluoromethanesulfonyl), under mild conditions with excellent yields and chemo-, regio-, and diastereoselectivities.

KW - Acid catalysis

KW - Cycloaddition

KW - Cyclobutanes

KW - Multiple bonds

KW - Used-ring systems

UR - http://www.scopus.com/inward/record.url?scp=70349922826&partnerID=8YFLogxK

U2 - 10.1002/anie.200902471

DO - 10.1002/anie.200902471

M3 - 文章

C2 - 19718730

AN - SCOPUS:70349922826

SN - 1433-7851

VL - 48

SP - 7232

EP - 7235

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 39

ER -

Acid-catalyzed intramolecular [2+2] Cycloaddition of ene-allenones: Facile access to bicyclo[n.2.0] frameworks

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this