Stereoselective intramolecular nicholas reaction using epoxides as nucleophiles |
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Authors: | Crisóstomo Fernando R P Martín Tomás Martín Víctor S |
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Institution: | Instituto Universitario de Bio-Orgánica "Antonio González", Universidad de La Laguna,C/Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain. |
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Abstract: | reaction: see text] The intramolecular nucleophilic attack of the epoxides on the exo-Co(2)(CO)(6)-propargylic cations provided cyclic ethers in good yields. The use of substrates with stereochemically defined oxiranes provided polysubstituted tetrahydropyrans and oxepanes with a high degree of stereocontrol. The cyclization is sensitive to the nature of the protecting group used at the primary alcohol, the use of tert-butyl carbonates being highly effective in terms of regioselectivity and yields. |
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