Highly stereocontrolled synthesis of fluorinated 2,6-trans dihydropyrans via Prins cyclization

Hai Qing Luo; Xu Hong Hu; Teck Peng Loh

doi:10.1016/j.tetlet.2009.12.068

Highly stereocontrolled synthesis of fluorinated 2,6-trans dihydropyrans via Prins cyclization

Hai Qing Luo, Xu Hong Hu, Teck Peng Loh^*

^*Corresponding author for this work

Nanyang Technological University

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

27 Citations (Scopus)

Abstract

A highly efficient method for the synthesis of fluorinated 2,6-trans dihydropyrans via BF₃·Et₂O-promoted Prins cyclization of allenic alcohols and aldehydes is developed. Various 2,6-trans fluorodihydropyrans are obtained in moderate to good yields with excellent diastereoselectivities.

Original language	English
Pages (from-to)	1041-1043
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2009.12.068
Publication status	Published - Feb 17 2010
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Allenic alcohols
BF·EtO
Fluorine chemistry
Prins cyclization
trans-Dihydropyrans

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10.1016/j.tetlet.2009.12.068

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title = "Highly stereocontrolled synthesis of fluorinated 2,6-trans dihydropyrans via Prins cyclization",

abstract = "A highly efficient method for the synthesis of fluorinated 2,6-trans dihydropyrans via BF3·Et2O-promoted Prins cyclization of allenic alcohols and aldehydes is developed. Various 2,6-trans fluorodihydropyrans are obtained in moderate to good yields with excellent diastereoselectivities.",

keywords = "Allenic alcohols, BF·EtO, Fluorine chemistry, Prins cyclization, trans-Dihydropyrans",

author = "Luo, {Hai Qing} and Hu, {Xu Hong} and Loh, {Teck Peng}",

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language = "English",

volume = "51",

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T1 - Highly stereocontrolled synthesis of fluorinated 2,6-trans dihydropyrans via Prins cyclization

AU - Luo, Hai Qing

AU - Hu, Xu Hong

AU - Loh, Teck Peng

PY - 2010/2/17

Y1 - 2010/2/17

N2 - A highly efficient method for the synthesis of fluorinated 2,6-trans dihydropyrans via BF3·Et2O-promoted Prins cyclization of allenic alcohols and aldehydes is developed. Various 2,6-trans fluorodihydropyrans are obtained in moderate to good yields with excellent diastereoselectivities.

AB - A highly efficient method for the synthesis of fluorinated 2,6-trans dihydropyrans via BF3·Et2O-promoted Prins cyclization of allenic alcohols and aldehydes is developed. Various 2,6-trans fluorodihydropyrans are obtained in moderate to good yields with excellent diastereoselectivities.

KW - Allenic alcohols

KW - BF·EtO

KW - Fluorine chemistry

KW - Prins cyclization

KW - trans-Dihydropyrans

UR - http://www.scopus.com/inward/record.url?scp=73649088301&partnerID=8YFLogxK

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U2 - 10.1016/j.tetlet.2009.12.068

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M3 - Article

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SP - 1041

EP - 1043

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

Highly stereocontrolled synthesis of fluorinated 2,6-trans dihydropyrans via Prins cyclization

Abstract

ASJC Scopus Subject Areas

Keywords

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