Stereoselective Synthesis of 3-Alkylated cis-1,2-Cyclobutanediols and Derivatives by Norrish-Yang Photocyclisation

Axel   G.   Griesbeck; Peter      Cygon; Johann      Lex

doi:10.2174/1570178043400613

Abstract

The photocyclisation of enantiomerically pure α-heteroatom-substituted β-methyl butyrophenones 1 results in Norrish II cleavage and in Norrish II / Yang cyclisation products, cyclobutanols 2, the latter being formed with excellent diastereoselectivities and with relative yields which were strongly depending on the Hbonding activity of the α-substituent.

Keywords: photocyclisation, norrish-yang reaction, butyrophenones, cyclobutanols

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Letters in Organic Chemistry

Title: Stereoselective Synthesis of 3-Alkylated cis-1,2-Cyclobutanediols and Derivatives by Norrish-Yang Photocyclisation

Volume: 1 Issue: 4

Author(s): Axel G. Griesbeck, Peter Cygon and Johann Lex

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Keywords: photocyclisation, norrish-yang reaction, butyrophenones, cyclobutanols

Abstract: The photocyclisation of enantiomerically pure α-heteroatom-substituted β-methyl butyrophenones 1 results in Norrish II cleavage and in Norrish II / Yang cyclisation products, cyclobutanols 2, the latter being formed with excellent diastereoselectivities and with relative yields which were strongly depending on the Hbonding activity of the α-substituent.

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Griesbeck G. Axel, Cygon Peter and Lex Johann, Stereoselective Synthesis of 3-Alkylated cis-1,2-Cyclobutanediols and Derivatives by Norrish-Yang Photocyclisation, Letters in Organic Chemistry 2004; 1 (4) . https://dx.doi.org/10.2174/1570178043400613