Stereoselective, one-pot, three-component synthesis of 4- aryltetrahydropyrans from epoxides via prins cyclization reaction

Kiran Indukuri; Somasekhar Bondalapati; Trimurtulu Kotipalli; Paramartha Gogoi; Anil K. Saikia

doi:10.1055/s-0031-1290080

Stereoselective, one-pot, three-component synthesis of 4- aryltetrahydropyrans from epoxides via prins cyclization reaction

Kiran Indukuri, Somasekhar Bondalapati, Trimurtulu Kotipalli, Paramartha Gogoi, Anil K. Saikia

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

16 Scopus citations

Abstract

A three-component, one-pot synthesis of 4-aryltetrahydropyrans from epoxides and homoallylic alcohols in arenes via Prins-Friedel-Crafts reaction, mediated by boron trifluoride etherate, has been developed. The reaction is diastereoselective and gives only all-cis diastereomers in moderate to good yields.

Original language	English
Pages (from-to)	233-238
Number of pages	6
Journal	Synlett
Issue number	2
DOIs	https://doi.org/10.1055/s-0031-1290080
State	Published - 4 Jan 2012
Externally published	Yes

Keywords

boron trifluoride etherate
epoxide
homoallylic alcohol
Prins cyclization
stereoselective
tetrahydropyran

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0031-1290080

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title = "Stereoselective, one-pot, three-component synthesis of 4- aryltetrahydropyrans from epoxides via prins cyclization reaction",

abstract = "A three-component, one-pot synthesis of 4-aryltetrahydropyrans from epoxides and homoallylic alcohols in arenes via Prins-Friedel-Crafts reaction, mediated by boron trifluoride etherate, has been developed. The reaction is diastereoselective and gives only all-cis diastereomers in moderate to good yields.",

keywords = "boron trifluoride etherate, epoxide, homoallylic alcohol, Prins cyclization, stereoselective, tetrahydropyran",

author = "Kiran Indukuri and Somasekhar Bondalapati and Trimurtulu Kotipalli and Paramartha Gogoi and Saikia, {Anil K.}",

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AU - Indukuri, Kiran

AU - Bondalapati, Somasekhar

AU - Kotipalli, Trimurtulu

AU - Gogoi, Paramartha

AU - Saikia, Anil K.

PY - 2012/1/4

Y1 - 2012/1/4

N2 - A three-component, one-pot synthesis of 4-aryltetrahydropyrans from epoxides and homoallylic alcohols in arenes via Prins-Friedel-Crafts reaction, mediated by boron trifluoride etherate, has been developed. The reaction is diastereoselective and gives only all-cis diastereomers in moderate to good yields.

AB - A three-component, one-pot synthesis of 4-aryltetrahydropyrans from epoxides and homoallylic alcohols in arenes via Prins-Friedel-Crafts reaction, mediated by boron trifluoride etherate, has been developed. The reaction is diastereoselective and gives only all-cis diastereomers in moderate to good yields.

KW - boron trifluoride etherate

KW - epoxide

KW - homoallylic alcohol

KW - Prins cyclization

KW - stereoselective

KW - tetrahydropyran

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DO - 10.1055/s-0031-1290080

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JF - Synlett

IS - 2

ER -

Stereoselective, one-pot, three-component synthesis of 4- aryltetrahydropyrans from epoxides via prins cyclization reaction

Abstract

Keywords

ASJC Scopus subject areas

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