Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 51, Pages 14175-14180Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408102
Keywords
alkyl carbenes; alkyl diazomethanes; C-H insertion; homogeneous catalysis; ruthenium
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Funding
- National Natural Science Foundation of China [NSFC 21272197]
- National Key Basic Research Program of China [2013CB834802]
- University Development Fund of HKU
- HKU
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With a ruthenium-porphyrin catalyst, alkyl diazomethanes generated in situ from N-tosylhydrazones efficiently underwent intramolecular C(sp(3))-H insertion of an alkyl carbene to give substituted tetrahydrofurans and pyrrolidines in up to 99% yield and with up to 99:1 cis selectivity. The reaction displays good tolerance of many functionalities, and the procedure is simple without the need for slow addition with a syringe pump. From a synthetic point of view, the C-H insertion of N-tosylhydrazones can be viewed as reductive coupling between a C=O bond and a C-H bond to form a new C-C bond, since N-tosylhydrazones can be readily prepared from carbonyl compounds. This reaction was successfully applied in a concise synthesis of (+/-)-pseudoheliotridane.
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