Regioselective synthesis of trichloromethyl-substituted salicylates and cyclohexenones by one-pot cyclizations of 1,3-bis(trimethylsilyloxy)buta-1,3- dienes

Sebastian Reimann; Alina Bunescu; Andranik Petrosyan; Muhammad Sharif; Silke Erfle; Constantin Mamat; Tariel V. Ghochikyan; Ashot S. Saghyan; Anke Spannenberg; Alexander Villinger; Peter Langer

doi:10.1002/hlca.201200595

Regioselective synthesis of trichloromethyl-substituted salicylates and cyclohexenones by one-pot cyclizations of 1,3-bis(trimethylsilyloxy)buta-1,3- dienes

Sebastian Reimann
, Alina Bunescu
, Andranik Petrosyan
, Muhammad Sharif
, Silke Erfle
, Constantin Mamat
, Tariel V. Ghochikyan
, Ashot S. Saghyan
, Anke Spannenberg
, Alexander Villinger
, Peter Langer^*

^*Corresponding author for this work

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

Abstract

A variety of 6-(trichloromethyl)salicylates (=2-hydroxy-6-(trichloromethyl) benzoates) were prepared by TiCl₄-mediated cyclization of 1,3-bis(trimethylsilyloxy)buta-1,3-dienes with 1,1,1-trichloro-4,4-dimethoxybut- 3-en-2-one. The employment of trimethylsilyl trifluoromethanesulfonate (Me ₃SiOTf) as Lewis acid resulted in the formation of trichloromethyl-substituted cyclohexenones. The cyclizations proceeded with good-to-very-good regioselectivities.

Original language	English
Pages (from-to)	1955-1967
Number of pages	13
Journal	Helvetica Chimica Acta
Volume	96
Issue number	10
DOIs	https://doi.org/10.1002/hlca.201200595
State	Published - Oct 2013
Externally published	Yes

Keywords

Arene formation
Cyclization reactions
Organochlorine compounds
Salicylates
Silyl enol ethers

ASJC Scopus subject areas

Catalysis
Biochemistry
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1002/hlca.201200595

Cite this

Reimann, S., Bunescu, A., Petrosyan, A., Sharif, M., Erfle, S., Mamat, C., Ghochikyan, T. V., Saghyan, A. S., Spannenberg, A., Villinger, A., & Langer, P. (2013). Regioselective synthesis of trichloromethyl-substituted salicylates and cyclohexenones by one-pot cyclizations of 1,3-bis(trimethylsilyloxy)buta-1,3- dienes. Helvetica Chimica Acta, 96(10), 1955-1967. https://doi.org/10.1002/hlca.201200595

@article{d9a2c8b207db470db2f2735e5d65670a,

title = "Regioselective synthesis of trichloromethyl-substituted salicylates and cyclohexenones by one-pot cyclizations of 1,3-bis(trimethylsilyloxy)buta-1,3- dienes",

abstract = "A variety of 6-(trichloromethyl)salicylates (=2-hydroxy-6-(trichloromethyl) benzoates) were prepared by TiCl4-mediated cyclization of 1,3-bis(trimethylsilyloxy)buta-1,3-dienes with 1,1,1-trichloro-4,4-dimethoxybut- 3-en-2-one. The employment of trimethylsilyl trifluoromethanesulfonate (Me 3SiOTf) as Lewis acid resulted in the formation of trichloromethyl-substituted cyclohexenones. The cyclizations proceeded with good-to-very-good regioselectivities.",

keywords = "Arene formation, Cyclization reactions, Organochlorine compounds, Salicylates, Silyl enol ethers",

author = "Sebastian Reimann and Alina Bunescu and Andranik Petrosyan and Muhammad Sharif and Silke Erfle and Constantin Mamat and Ghochikyan, \{Tariel V.\} and Saghyan, \{Ashot S.\} and Anke Spannenberg and Alexander Villinger and Peter Langer",

year = "2013",

month = oct,

doi = "10.1002/hlca.201200595",

language = "English",

volume = "96",

pages = "1955--1967",

journal = "Helvetica Chimica Acta",

issn = "0018-019X",

publisher = "Wiley-Blackwell",

number = "10",

}

Reimann, S, Bunescu, A, Petrosyan, A, Sharif, M, Erfle, S, Mamat, C, Ghochikyan, TV, Saghyan, AS, Spannenberg, A, Villinger, A & Langer, P 2013, 'Regioselective synthesis of trichloromethyl-substituted salicylates and cyclohexenones by one-pot cyclizations of 1,3-bis(trimethylsilyloxy)buta-1,3- dienes', Helvetica Chimica Acta, vol. 96, no. 10, pp. 1955-1967. https://doi.org/10.1002/hlca.201200595

TY - JOUR

T1 - Regioselective synthesis of trichloromethyl-substituted salicylates and cyclohexenones by one-pot cyclizations of 1,3-bis(trimethylsilyloxy)buta-1,3- dienes

AU - Reimann, Sebastian

AU - Bunescu, Alina

AU - Petrosyan, Andranik

AU - Sharif, Muhammad

AU - Erfle, Silke

AU - Mamat, Constantin

AU - Ghochikyan, Tariel V.

AU - Saghyan, Ashot S.

AU - Spannenberg, Anke

AU - Villinger, Alexander

AU - Langer, Peter

PY - 2013/10

Y1 - 2013/10

N2 - A variety of 6-(trichloromethyl)salicylates (=2-hydroxy-6-(trichloromethyl) benzoates) were prepared by TiCl4-mediated cyclization of 1,3-bis(trimethylsilyloxy)buta-1,3-dienes with 1,1,1-trichloro-4,4-dimethoxybut- 3-en-2-one. The employment of trimethylsilyl trifluoromethanesulfonate (Me 3SiOTf) as Lewis acid resulted in the formation of trichloromethyl-substituted cyclohexenones. The cyclizations proceeded with good-to-very-good regioselectivities.

AB - A variety of 6-(trichloromethyl)salicylates (=2-hydroxy-6-(trichloromethyl) benzoates) were prepared by TiCl4-mediated cyclization of 1,3-bis(trimethylsilyloxy)buta-1,3-dienes with 1,1,1-trichloro-4,4-dimethoxybut- 3-en-2-one. The employment of trimethylsilyl trifluoromethanesulfonate (Me 3SiOTf) as Lewis acid resulted in the formation of trichloromethyl-substituted cyclohexenones. The cyclizations proceeded with good-to-very-good regioselectivities.

KW - Arene formation

KW - Cyclization reactions

KW - Organochlorine compounds

KW - Salicylates

KW - Silyl enol ethers

UR - https://www.scopus.com/pages/publications/84886937295

U2 - 10.1002/hlca.201200595

DO - 10.1002/hlca.201200595

M3 - Article

AN - SCOPUS:84886937295

SN - 0018-019X

VL - 96

SP - 1955

EP - 1967

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 10

ER -

Regioselective synthesis of trichloromethyl-substituted salicylates and cyclohexenones by one-pot cyclizations of 1,3-bis(trimethylsilyloxy)buta-1,3- dienes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this