Intramolecular Nicholas reaction: stereoselective synthesis of 5-alkynylproline derivatives |
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| Authors: | Hernández J Nicolás Ramírez Miguel A Rodríguez Matías L Martín Víctor S |
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| Affiliation: | Instituto Universitario de Bio-Orgánica Antonio González Universidad de La Laguna, La Laguna, Tenerife, Spain. |
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| Abstract: | The intramolecular Nicholas reaction of propargylic alcohols derived from N, N-acyl-diprotected omega-semialdehydes obtained from glutamic acid provided stereoselectively 5-alkynylproline derivatives. The suitable choice of the N-protecting group (tosyl or benzoyl derivative) permitted control of the stereochemistry during the ring formation. Semiempirical calculations of the species involved in the cyclization support the observed stereochemistry. |
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