Journal
TETRAHEDRON LETTERS
Volume 61, Issue 41, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2020.152377
Keywords
[5+2] cycloadditions; Chiral auxiliary; Asymmetric; Organic synthesis
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Funding
- American Chemical Society Petroleum Research Fund (PRF) [52391-UNI1]
- National Science Foundation [CHE-0722385, CHE-1039689, CHE-1337497, CHE1565644]
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Intramolecular oxidopyrylium-based [5 + 2] cycloadditions utilizing chiral auxiliaries were investigated. Both acetoxypyranones and silyloxypyrones were employed and sulfinimines, oxazolidinones, hydrazones, and chiral enamines were explored. Carbonyl-based auxiliaries gave low selectivity, but enamines afforded excellent diastereoselectivity. Overall, facial selectivity varied significantly providing insight regarding the scope and limitation of chiral auxiliary-based oxidopyrylium-alkene [5 + 2] cycloadditions. (C) 2020 Elsevier Ltd. All rights reserved.
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