期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 19, 页码 4940-4944出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402170
关键词
cyclization; decarboxylation; heterocycles; organocatalysis; synthetic methods
资金
- NSF [CHE-1057569]
- National Science Foundation of China [21372073]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1057569] Funding Source: National Science Foundation
An asymmetric two-step approach to chiral bridged tricyclic benzopyrans, core structures featured in various natural products, is described. In the synthesis, an unprecedented enantioselective catalytic decarboxylative Diels-Alder reaction is developed using readily available coumarin-3-carboxylic acids and aldehydes as reactants under mild reaction conditions. Notably, the decarboxylation-assisted release of the catalyst enables the process to proceed efficiently with high enantio- and diastereoselectivity. Furthermore, a one-pot procedure for either a LiAlH4- or NaBH4-mediated reduction with subsequent acid-catalyzed intramolecular cyclization of the Diels-Alder adducts was identified for the efficient formation of the chiral bridged tricyclic benzopyrans.
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