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Synlett 2001; 2001(Special Issue): 0900-0903
DOI: 10.1055/s-2001-14661
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A New Photolabile Linker for the Photoactivation of Carboxyl Groups

K. C. Nicolaou* , Brian S. Safina, Nicolas Winssinger
  • *Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, California 92037, USA; Fax + 1 (858) 7 84 24 69; E-mail: kcn@scripps.edu
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Publication Date:
31 December 2001 (online)

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A new photolabile linker enabling nucleophilic cleavage of a carboxyl functionality upon irradiation with UV light (> 290 nm) was developed. When the photocleavage is carried out in the presence of primary or secondary amines, amides are obtained in high yields and purities, while the intramolecular version of this reaction leads to heterocycles via a cyclorelease mechanism.

solid phase synthesis - photolabile linker - amides - cyclizations

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