Regio- and diastereoselectivity studies on the photocycloaddition of ketene diethyl acetal to chiral 2(5H)-furanones

Albert Rustullet; Marta Racamonde; Ramon Alibés; Pedro de March; Marta Figueredo; Josep Font

doi:10.1016/j.tet.2008.07.082

Regio- and diastereoselectivity studies on the photocycloaddition of ketene diethyl acetal to chiral 2(5H)-furanones

Albert Rustullet, Marta Racamonde, Ramon Alibés, Pedro de March, Marta Figueredo, Josep Font

Department of Chemistry

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

8 Citations (Scopus)

Abstract

The photochemical [2+2] cycloaddition of 1,1-diethoxyethylene to chiral 2(5H)-furanones is investigated. The effect of the substituents of the lactone and the polarity of the solvents on the chemical yield, regioselectivity, and facial diastereoselectivity is evaluated. The reactions in ether proceed with excellent regioselectivity and good yields. Hydrolysis of the ketal group of the major cycloadducts afforded enantiopure cyclobutanones fused to γ-lactones. © 2008 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	9442-9447
Journal	Tetrahedron
Volume	64
Issue number	40
DOIs	https://doi.org/10.1016/j.tet.2008.07.082
Publication status	Published - 29 Sep 2008

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title = "Regio- and diastereoselectivity studies on the photocycloaddition of ketene diethyl acetal to chiral 2(5H)-furanones",

abstract = "The photochemical [2+2] cycloaddition of 1,1-diethoxyethylene to chiral 2(5H)-furanones is investigated. The effect of the substituents of the lactone and the polarity of the solvents on the chemical yield, regioselectivity, and facial diastereoselectivity is evaluated. The reactions in ether proceed with excellent regioselectivity and good yields. Hydrolysis of the ketal group of the major cycloadducts afforded enantiopure cyclobutanones fused to γ-lactones. {\textcopyright} 2008 Elsevier Ltd. All rights reserved.",

author = "Albert Rustullet and Marta Racamonde and Ramon Alib{\'e}s and {de March}, Pedro and Marta Figueredo and Josep Font",

year = "2008",

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day = "29",

doi = "10.1016/j.tet.2008.07.082",

language = "English",

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TY - JOUR

T1 - Regio- and diastereoselectivity studies on the photocycloaddition of ketene diethyl acetal to chiral 2(5H)-furanones

AU - Rustullet, Albert

AU - Racamonde, Marta

AU - Alibés, Ramon

AU - de March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

PY - 2008/9/29

Y1 - 2008/9/29

N2 - The photochemical [2+2] cycloaddition of 1,1-diethoxyethylene to chiral 2(5H)-furanones is investigated. The effect of the substituents of the lactone and the polarity of the solvents on the chemical yield, regioselectivity, and facial diastereoselectivity is evaluated. The reactions in ether proceed with excellent regioselectivity and good yields. Hydrolysis of the ketal group of the major cycloadducts afforded enantiopure cyclobutanones fused to γ-lactones. © 2008 Elsevier Ltd. All rights reserved.

AB - The photochemical [2+2] cycloaddition of 1,1-diethoxyethylene to chiral 2(5H)-furanones is investigated. The effect of the substituents of the lactone and the polarity of the solvents on the chemical yield, regioselectivity, and facial diastereoselectivity is evaluated. The reactions in ether proceed with excellent regioselectivity and good yields. Hydrolysis of the ketal group of the major cycloadducts afforded enantiopure cyclobutanones fused to γ-lactones. © 2008 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tet.2008.07.082

DO - 10.1016/j.tet.2008.07.082

M3 - Article

VL - 64

SP - 9442

EP - 9447

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 40

ER -