Lewis acid catalyzed diels - alder reactions of 1,2-naphthoquinones

Danny M. Gelman; Craig M. Forsyth; Patrick Perlmutter

doi:10.1021/ol9021047

Lewis acid catalyzed diels - alder reactions of 1,2-naphthoquinones

Danny M. Gelman, Craig M. Forsyth, Patrick Perlmutter

School of Chemistry

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

20 Citations (Scopus)

Abstract

The use of BF₃-OEt₂ catalysis in Diels-Alder reactions of 3,4-unsubstituted 1,2-naphthoquinones provides direct access to cistetrahydrophenanthrene derivatives in good to excellent yields (66-99%) without rapid adduct aromatization commonly associated with corresponding thermal processes.

Original language	English
Pages (from-to)	4958-4960
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	21
DOIs	https://doi.org/10.1021/ol9021047
Publication status	Published - 5 Nov 2009

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10.1021/ol9021047

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@article{b0b87e07606e4442b8d9e19b3a288d34,

title = "Lewis acid catalyzed diels - alder reactions of 1,2-naphthoquinones",

abstract = "The use of BF3-OEt2 catalysis in Diels-Alder reactions of 3,4-unsubstituted 1,2-naphthoquinones provides direct access to cistetrahydrophenanthrene derivatives in good to excellent yields (66-99\%) without rapid adduct aromatization commonly associated with corresponding thermal processes.",

author = "Gelman, \{Danny M.\} and Forsyth, \{Craig M.\} and Patrick Perlmutter",

year = "2009",

month = nov,

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doi = "10.1021/ol9021047",

language = "English",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

number = "21",

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T1 - Lewis acid catalyzed diels - alder reactions of 1,2-naphthoquinones

AU - Gelman, Danny M.

AU - Forsyth, Craig M.

AU - Perlmutter, Patrick

PY - 2009/11/5

Y1 - 2009/11/5

N2 - The use of BF3-OEt2 catalysis in Diels-Alder reactions of 3,4-unsubstituted 1,2-naphthoquinones provides direct access to cistetrahydrophenanthrene derivatives in good to excellent yields (66-99%) without rapid adduct aromatization commonly associated with corresponding thermal processes.

AB - The use of BF3-OEt2 catalysis in Diels-Alder reactions of 3,4-unsubstituted 1,2-naphthoquinones provides direct access to cistetrahydrophenanthrene derivatives in good to excellent yields (66-99%) without rapid adduct aromatization commonly associated with corresponding thermal processes.

UR - https://www.scopus.com/pages/publications/70350666644

U2 - 10.1021/ol9021047

DO - 10.1021/ol9021047

M3 - Article

AN - SCOPUS:70350666644

SN - 1523-7060

VL - 11

SP - 4958

EP - 4960

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Lewis acid catalyzed diels - alder reactions of 1,2-naphthoquinones

Abstract

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