期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 46, 页码 13706-13710出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506559
关键词
annulation; heterocycles; reaction mechanisms; synthetic methods; total synthesis
资金
- NSF [CHE-1266365]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1565500] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1266365] Funding Source: National Science Foundation
An asymmetric [3+2] annulation reaction to form 3-pyrroline products is reported. Upon treatment with lithium diisopropylamide, readily available ethyl 4-bromocrotonate is deprotonated and trapped with Ellman imines selectively at the -position to yield enantiopure 3-pyrroline products. This new method is compatible with aryl, alkyl, and vinyl imines. The efficacy of the method is showcased by short asymmetric total syntheses of (-)-supinidine, (-)-isoretronecanol, and (+)-elacomine. This novel annulation approach also works for an aldehyde, thus providing access to a 2,5-dihydrofuran product in a single step from simple precursors. By modifying the structure of the carbanion nucleophile, an asymmetric vinylogous aza-Darzens reaction can be realized.
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