Journal
TETRAHEDRON
Volume 76, Issue 38, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131461
Keywords
Stereoselective synthesis; Chiral auxiliary; Benzyne chemistry; DFT calculations; Aporphine alkaloids
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Funding
- Sao Paulo Research Foundation (FAPESP) [2009/54011-8, 2017/21990-0]
- National Council for Scientific and Technological Development (CNPq)
- Coordination for the Improvement of Higher Education Personnel (CAPES)
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Total syntheses of (S)- and (R)-nuciferine were accomplished through approach involving diastereoselective reaction between a chiral dihydroisoquinoline enamide and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate promoted by CsF, affording a separable mixture of diastereoisomers, which provided (S)- and (R)-nuciferine via simple and efficient transformations. (C) 2020 Elsevier Ltd. All rights reserved.
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