Selectivity control in lewis acid catalyzed regiodivergent tandem cationic cyclization/ring expansion terminated by pinacol rearrangement

Lu Liu; Junliang Zhang

doi:10.1002/anie.200901628

Selectivity control in lewis acid catalyzed regiodivergent tandem cationic cyclization/ring expansion terminated by pinacol rearrangement

Lu Liu
, Junliang Zhang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

79 Scopus citations

Abstract

Catalyst is key: The title reaction sequence has been carried out on 1 in the presence of AgSbF₆ (5 mol %) in DCE or In(OTf)₃ (5 mol %) with MeOH (4 equiv) to afford 2 or 3, respectively, in up to >20:1 ratio (see scheme; DCE=1,2-dichloroethane, Tf=trifluoromethanesulfonyl).

Original language	English
Pages (from-to)	6093-6096
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	33
DOIs	https://doi.org/10.1002/anie.200901628
State	Published - 2009

Keywords

Cyclization
Domino reactions
Lewis acids
Pinacol rearrangement
Regioselectivity

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@article{c939811ebf22423c894d592724232d7f,

title = "Selectivity control in lewis acid catalyzed regiodivergent tandem cationic cyclization/ring expansion terminated by pinacol rearrangement",

abstract = "Catalyst is key: The title reaction sequence has been carried out on 1 in the presence of AgSbF6 (5 mol \%) in DCE or In(OTf)3 (5 mol \%) with MeOH (4 equiv) to afford 2 or 3, respectively, in up to >20:1 ratio (see scheme; DCE=1,2-dichloroethane, Tf=trifluoromethanesulfonyl).",

keywords = "Cyclization, Domino reactions, Lewis acids, Pinacol rearrangement, Regioselectivity",

author = "Lu Liu and Junliang Zhang",

year = "2009",

doi = "10.1002/anie.200901628",

language = "英语",

volume = "48",

pages = "6093--6096",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "33",

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TY - JOUR

T1 - Selectivity control in lewis acid catalyzed regiodivergent tandem cationic cyclization/ring expansion terminated by pinacol rearrangement

AU - Liu, Lu

AU - Zhang, Junliang

PY - 2009

Y1 - 2009

N2 - Catalyst is key: The title reaction sequence has been carried out on 1 in the presence of AgSbF6 (5 mol %) in DCE or In(OTf)3 (5 mol %) with MeOH (4 equiv) to afford 2 or 3, respectively, in up to >20:1 ratio (see scheme; DCE=1,2-dichloroethane, Tf=trifluoromethanesulfonyl).

AB - Catalyst is key: The title reaction sequence has been carried out on 1 in the presence of AgSbF6 (5 mol %) in DCE or In(OTf)3 (5 mol %) with MeOH (4 equiv) to afford 2 or 3, respectively, in up to >20:1 ratio (see scheme; DCE=1,2-dichloroethane, Tf=trifluoromethanesulfonyl).

KW - Cyclization

KW - Domino reactions

KW - Lewis acids

KW - Pinacol rearrangement

KW - Regioselectivity

UR - https://www.scopus.com/pages/publications/70349909806

U2 - 10.1002/anie.200901628

DO - 10.1002/anie.200901628

M3 - 文章

AN - SCOPUS:70349909806

SN - 1433-7851

VL - 48

SP - 6093

EP - 6096

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 33

ER -

Selectivity control in lewis acid catalyzed regiodivergent tandem cationic cyclization/ring expansion terminated by pinacol rearrangement

Abstract

Keywords

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