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Synthesis 2018; 50(06): 1307-1314
DOI: 10.1055/s-0036-1591724
DOI: 10.1055/s-0036-1591724
paper
Brønsted Acid Catalyzed Domino 1,6-Addition/Intramolecular Cyclization Reactions: Diastereoselective Synthesis of Dihydrocoumarin Frameworks
Autor*innen
We much appreciate the financial support from NSFC (21702077), the Natural Science Foundation of Jiangsu Province (BK20170227), PAPD, TAPP and the Undergraduate Student Project of Jiangsu Province.
Weitere Informationen
Publikationsverlauf
Received: 19. September 2017
Accepted after revision: 20. Oktober 2017
Publikationsdatum:
21. November 2017 (online)
Abstract
An efficient domino 1,6-addition/intramolecular cyclization reaction between para-quinone methides (p-QMs) and azlactones under Brønsted acid catalysis was established. A series of highly functionalized dihydrocoumarins were constructed in good to excellent yields (up to 96%) with excellent diastereoselectivities (all >20:1 d.r.). In this process, the Brønsted acid plays a crucial role not only in activating the two substrates, but also in controlling the diastereoselectivity of the reaction via hydrogen-bonding interactions. In addition, this protocol demonstrates the great practicability of utilizing p-QMs in domino reactions.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591724.
- Supporting Information (PDF) (opens in new window)
-
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For selected examples, see:
For selected reviews, see:
For selected examples, see:
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For related reviews, see:
For selected examples, see:
For selected reviews on domino reactions, see:
For selected examples, see: