Synthesis of Spiro annelated isochromanones by ring expansion of benzocyclobutenones in the presence of lithium diisopropylphosphide

Stefanie Kohser; Krishna Gopal Dongol; Holger Butenschön

doi:10.3987/com-07-s(w)11

Synthesis of Spiro annelated isochromanones by ring expansion of benzocyclobutenones in the presence of lithium diisopropylphosphide

Stefanie Kohser^*
, Krishna Gopal Dongol
, Holger Butenschön

^*Corresponding author for this work

Institute of Organic Chemistry

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

Abstract

spiro-Annelated isochromanones are prepared by treatment of benzo-cyclobutenone with lithium diisopropylphosphide - borane adduct (LDP-BH₃), which is easily accessible by metalation of the air stable diisopropylphos-phane-borane adduct. The reaction takes place at very mild reaction conditions and involves an oxyanion driven ring opening. As a substituted example the synthesis of the first trifluoromethyl-substituted isochromanone derivative is reported.

Original language	English
Pages (from-to)	339-350
Number of pages	12
Journal	Heterocycles
Volume	74
Issue number	C
DOIs	https://doi.org/10.3987/com-07-s(w)11
Publication status	Published - 27 Jul 2007

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "spiro-Annelated isochromanones are prepared by treatment of benzo-cyclobutenone with lithium diisopropylphosphide - borane adduct (LDP-BH3), which is easily accessible by metalation of the air stable diisopropylphos-phane-borane adduct. The reaction takes place at very mild reaction conditions and involves an oxyanion driven ring opening. As a substituted example the synthesis of the first trifluoromethyl-substituted isochromanone derivative is reported.",

author = "Stefanie Kohser and \{Gopal Dongol\}, Krishna and Holger Butensch{\"o}n",

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T1 - Synthesis of Spiro annelated isochromanones by ring expansion of benzocyclobutenones in the presence of lithium diisopropylphosphide

AU - Kohser, Stefanie

AU - Gopal Dongol, Krishna

AU - Butenschön, Holger

PY - 2007/7/27

Y1 - 2007/7/27

N2 - spiro-Annelated isochromanones are prepared by treatment of benzo-cyclobutenone with lithium diisopropylphosphide - borane adduct (LDP-BH3), which is easily accessible by metalation of the air stable diisopropylphos-phane-borane adduct. The reaction takes place at very mild reaction conditions and involves an oxyanion driven ring opening. As a substituted example the synthesis of the first trifluoromethyl-substituted isochromanone derivative is reported.

AB - spiro-Annelated isochromanones are prepared by treatment of benzo-cyclobutenone with lithium diisopropylphosphide - borane adduct (LDP-BH3), which is easily accessible by metalation of the air stable diisopropylphos-phane-borane adduct. The reaction takes place at very mild reaction conditions and involves an oxyanion driven ring opening. As a substituted example the synthesis of the first trifluoromethyl-substituted isochromanone derivative is reported.

UR - https://www.scopus.com/pages/publications/40749101753

U2 - 10.3987/com-07-s(w)11

DO - 10.3987/com-07-s(w)11

M3 - Article

AN - SCOPUS:40749101753

SN - 0385-5414

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SP - 339

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JO - Heterocycles

JF - Heterocycles

IS - C

ER -

Synthesis of Spiro annelated isochromanones by ring expansion of benzocyclobutenones in the presence of lithium diisopropylphosphide

Abstract

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