Photochemical [2 + 2] cycloaddition of acetylene to chiral 2(5H)-furanones

Ramon Alibés; Pedro De March; Marta Figueredo; Josep Font; Xiaolin Fu; Marta Racamonde; Ángel Álvarez-Larena; Juan F. Piniella

doi:10.1021/jo0264731

Photochemical [2 + 2] cycloaddition of acetylene to chiral 2(5H)-furanones

Ramon Alibés, Pedro De March, Marta Figueredo, Josep Font, Xiaolin Fu, Marta Racamonde, Ángel Álvarez-Larena, Juan F. Piniella

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

24 Citations (Scopus)

Abstract

The [2 + 2] photocycloaddition of acetylene to chiral 2(5H)-furanones was investigated. The influence on the chemical yield and facial diastereoselectivity of the substituent at the stereogenic center and also the effect of a 4-methyl group were evaluated. A mechanistic proposal based on a simple theoretical conformational analysis is presented. Using a C2-symmetric bis(lactone) as the substrate, a diastereomeric excess higher than 98% was found.

Original language	English
Pages (from-to)	1283-1289
Journal	Journal of Organic Chemistry
Volume	68
Issue number	4
DOIs	https://doi.org/10.1021/jo0264731
Publication status	Published - 21 Feb 2003

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title = "Photochemical [2 + 2] cycloaddition of acetylene to chiral 2(5H)-furanones",

abstract = "The [2 + 2] photocycloaddition of acetylene to chiral 2(5H)-furanones was investigated. The influence on the chemical yield and facial diastereoselectivity of the substituent at the stereogenic center and also the effect of a 4-methyl group were evaluated. A mechanistic proposal based on a simple theoretical conformational analysis is presented. Using a C2-symmetric bis(lactone) as the substrate, a diastereomeric excess higher than 98% was found.",

author = "Ramon Alib{\'e}s and {De March}, Pedro and Marta Figueredo and Josep Font and Xiaolin Fu and Marta Racamonde and {\'A}ngel {\'A}lvarez-Larena and Piniella, {Juan F.}",

year = "2003",

month = feb,

day = "21",

doi = "10.1021/jo0264731",

language = "English",

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Photochemical [2 + 2] cycloaddition of acetylene to chiral 2(5H)-furanones. / Alibés, Ramon; De March, Pedro; Figueredo, Marta; Font, Josep; Fu, Xiaolin; Racamonde, Marta; Álvarez-Larena, Ángel; Piniella, Juan F.

In: Journal of Organic Chemistry, Vol. 68, No. 4, 21.02.2003, p. 1283-1289.

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

TY - JOUR

T1 - Photochemical [2 + 2] cycloaddition of acetylene to chiral 2(5H)-furanones

AU - Alibés, Ramon

AU - De March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

AU - Fu, Xiaolin

AU - Racamonde, Marta

AU - Álvarez-Larena, Ángel

AU - Piniella, Juan F.

PY - 2003/2/21

Y1 - 2003/2/21

N2 - The [2 + 2] photocycloaddition of acetylene to chiral 2(5H)-furanones was investigated. The influence on the chemical yield and facial diastereoselectivity of the substituent at the stereogenic center and also the effect of a 4-methyl group were evaluated. A mechanistic proposal based on a simple theoretical conformational analysis is presented. Using a C2-symmetric bis(lactone) as the substrate, a diastereomeric excess higher than 98% was found.

AB - The [2 + 2] photocycloaddition of acetylene to chiral 2(5H)-furanones was investigated. The influence on the chemical yield and facial diastereoselectivity of the substituent at the stereogenic center and also the effect of a 4-methyl group were evaluated. A mechanistic proposal based on a simple theoretical conformational analysis is presented. Using a C2-symmetric bis(lactone) as the substrate, a diastereomeric excess higher than 98% was found.

U2 - 10.1021/jo0264731

DO - 10.1021/jo0264731

M3 - Article

VL - 68

SP - 1283

EP - 1289

IS - 4

ER -