Stereoselective [2+2] photocycloaddition of acetylene to chiral 2(5H)-furanones

Ramon Alibés; Pedro De March; Marta Figueredo; Josep Font; Marta Racamonde

doi:10.1016/S0040-4039(01)01374-0

Stereoselective [2+2] photocycloaddition of acetylene to chiral 2(5H)-furanones

Ramon Alibés, Pedro De March, Marta Figueredo, Josep Font, Marta Racamonde

Department of Chemistry

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

13 Citations (Scopus)

Abstract

The photochemical [2+2] cycloaddition of acetylene to chiral 2(5H)-furanones is investigated. The effect of the substituent at the stereogenic center of the lactone on the chemical yield and facial diastereoselectivity is evaluated. Using a C2-symmetric bis-lactone as substrate, a diastereomeric excess higher than 98% is found. © 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	6695-6697
Journal	Tetrahedron Letters
Volume	42
Issue number	38
DOIs	https://doi.org/10.1016/S0040-4039(01)01374-0
Publication status	Published - 17 Sept 2001

Keywords

Acetylene
Cyclobutenes
Diastereoselection
Furanones
Photochemical cycloadditions

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10.1016/S0040-4039(01)01374-0

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

abstract = "The photochemical [2+2] cycloaddition of acetylene to chiral 2(5H)-furanones is investigated. The effect of the substituent at the stereogenic center of the lactone on the chemical yield and facial diastereoselectivity is evaluated. Using a C2-symmetric bis-lactone as substrate, a diastereomeric excess higher than 98% is found. {\textcopyright} 2001 Elsevier Science Ltd. All rights reserved.",

keywords = "Acetylene, Cyclobutenes, Diastereoselection, Furanones, Photochemical cycloadditions",

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

year = "2001",

month = sep,

day = "17",

doi = "10.1016/S0040-4039(01)01374-0",

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pages = "6695--6697",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Stereoselective [2+2] photocycloaddition of acetylene to chiral 2(5H)-furanones

AU - Alibés, Ramon

AU - De March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

AU - Racamonde, Marta

PY - 2001/9/17

Y1 - 2001/9/17

N2 - The photochemical [2+2] cycloaddition of acetylene to chiral 2(5H)-furanones is investigated. The effect of the substituent at the stereogenic center of the lactone on the chemical yield and facial diastereoselectivity is evaluated. Using a C2-symmetric bis-lactone as substrate, a diastereomeric excess higher than 98% is found. © 2001 Elsevier Science Ltd. All rights reserved.

AB - The photochemical [2+2] cycloaddition of acetylene to chiral 2(5H)-furanones is investigated. The effect of the substituent at the stereogenic center of the lactone on the chemical yield and facial diastereoselectivity is evaluated. Using a C2-symmetric bis-lactone as substrate, a diastereomeric excess higher than 98% is found. © 2001 Elsevier Science Ltd. All rights reserved.

KW - Acetylene

KW - Cyclobutenes

KW - Diastereoselection

KW - Furanones

KW - Photochemical cycloadditions

U2 - 10.1016/S0040-4039(01)01374-0

DO - 10.1016/S0040-4039(01)01374-0

M3 - Article

SN - 0040-4039

VL - 42

SP - 6695

EP - 6697

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Stereoselective [2+2] photocycloaddition of acetylene to chiral 2(5H)-furanones

Abstract

Keywords

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