期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 17, 页码 4647-4651出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201801110
关键词
cycloaddition; enantioselectivity; natural products; small ring systems; total synthesis
资金
- Indiana University
- National Institutes of Health [R01GM110131]
- Deutsche Forschungsgemeinschaft [W1 4933/1-1]
The first synthesis of hebelophylleneE is presented, along with assignment of its previously unknown relative configuration through synthesis of epi-ent-hebelophylleneE. Development of a catalytic enantioselective [2+2] cycloaddition of alkenes and allenoates provides access to the required chiral geminal dimethylcyclobutanes. Key to its success is the identification of a novel oxazaborolidine catalyst which promotes the cycloaddition in high enantioselectivities with good functional-group tolerance (9 examples, up to 97:3 e.r.). Thus, a late-stage cycloaddition using a fully functionalized alkene, followed by a diastereoselective reduction allows a concise entry to this class of natural products.
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