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Nitromethane as a Carbanion Source for Domino Benzoannulation with Ynones: One‐Pot Synthesis of Polyfunctional Naphthalenes and a Total Synthesis of Macarpine
Author(s) -
Singh Shweta,
Samineni Ramesh,
Pabbaraja Srihari,
Mehta Goverdhan
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810652
Subject(s) - carbanion , regioselectivity , nitromethane , chemistry , domino , alicyclic compound , substituent , leaving group , combinatorial chemistry , organic chemistry , catalysis
A one‐pot, transition‐metal‐free, domino Michael/S N Ar protocol of general applicability has been devised for the regioselective synthesis of polyfunctional naphthalenes by employing nitromethane and ortho ‐haloaryl ynones. Utilization of nitromethane as a one carbon carbanion source that is incorporated into a variety of ynones, ends up as an aromatic nitro substituent. The application of this domino process towards a total synthesis of the polycyclic alkaloid macarpine demonstrate for the efficacy of this methodology. The conceptually simple approach to affect regioselective, multifunctional benzoannulation of ynones displays wide substrate scope and functional‐group tolerance and has been implemented with substituted nitromethanes, as well as with alicyclic o ‐haloynones.