We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Enantioselective Synthesis of Phthalides and Isochromanones via Heck–Matsuda Arylation of Dihydrofurans.
- Authors
Kattela, Shivashankar; de Lucca, Emilio C.; Correia, Carlos Roque D.
- Abstract
In this communication, the enantioselective synthesis of phthalides and isochromanones is described through a new palladium‐catalyzed Heck–Matsuda arylation/NaBH4‐reduction/lactonization sequence of 2,3‐ and 2,5‐dihydrofurans in good overall yields and excellent enantioselectivities (up to 98:2 er). This expeditious synthesis of chiral Heck lactol intermediates allowed the diversification of the strategy to obtain medicinally relevant chiral lactones, amines, and olefins. The natural product 3‐butylphthalide was obtained in three steps with an overall yield of 33 % yield in 98:2 er. Transformer: A new palladium‐catalyzed Heck–Matsuda arylation of dihydrofurans coupled with NaBH4‐reduction/lactonization furnished phthalides and isochromanones in good overall yields and excellent enantioselectivity (up to 98:2 er). The DHF moiety functions as a complementary source of functionalities and the point of creation of the new stereogenic center.
- Subjects
ENANTIOSELECTIVE catalysis; PHTHALIDES; DIHYDROFURANS; HECK reaction; ARYLATION
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 67, p17691
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201804958