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Highly Chemoselective and Stereoselective Synthesis of Z-Enol Silanes
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Abstract
Three-component nickel-catalyzed couplings of enals, alkynes, and silanes have been developed as a new entry to enol silanes. The enol silane and a trisubstituted alkene are both formed with >98:2 stereoselectivity, and the reaction tolerates a broad range of functionality including aldehydes, ketones, esters, free hydroxyls, and basic secondary amines. A mechanistic pathway involving the formation of a metallacycle that possesses an η1 nickel O-enolate motif explains the high level of stereoselection.
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
Enone–Alkyne Reductive Coupling: A Versatile Entry to Substituted Pyrroles
Benjamin B. Thompson and John MontgomeryOrganic Letters2011 Article ASAPEnone–Alkyne Reductive Coupling: A Versatile Entry to Substituted Pyrroles
Benjamin B. Thompson and John MontgomeryOrganic Letters2011 Article ASAPThe reductive coupling of enones or enals with alkynes, followed by olefin oxidative cleavage and Paal–Knorr cyclization, provides a versatile entry to a variety of pyrrole frameworks. A number of limitations of alternate entries to the requisite 1,4-...
Enantioselective Synthesis of β-Substituted Cyclic Ketones via Cobalt-Catalyzed Asymmetric Reductive Coupling of Alkynes with Alkenes
Chu-Hung Wei, Subramaniyan Mannathan, and Chien-Hong ChengJournal of the American Chemical Society2011 Article ASAPEnantioselective Synthesis of β-Substituted Cyclic Ketones via Cobalt-Catalyzed Asymmetric Reductive Coupling of Alkynes with Alkenes
Chu-Hung Wei, Subramaniyan Mannathan, and Chien-Hong ChengJournal of the American Chemical Society2011 Article ASAPA CoI2/(R)-BINAP, Zn, ZnI2, H2O system efficiently catalyzes the intermolecular asymmetric reductive coupling of alkynes with cyclic enones to afford highly regio- and enantioselective β-alkenyl cyclic ketones. A possible mechanism that involves the ...
Evolution of Efficient Strategies for Enone−Alkyne and Enal−Alkyne Reductive Couplings
Wei Li, Ananda Herath and John MontgomeryJournal of the American Chemical Society2009 131 (46), 17024-17029Evolution of Efficient Strategies for Enone−Alkyne and Enal−Alkyne Reductive Couplings
Wei Li, Ananda Herath and John MontgomeryJournal of the American Chemical Society2009 131 (46), 17024-17029Strategies for the reductive coupling of enones or enals with alkynes have been developed. The reducing agents employed include organozincs, organoboranes, organosilanes, and methanol. The latter of these strategies is simple, cost-effective, and tolerant ...
Nickel-Catalyzed Cycloaddition of Salicylic Acid Ketals to Alkynes via Elimination of Ketones
Akihiro Ooguri, Kenichiro Nakai, Takuya Kurahashi and Seijiro MatsubaraJournal of the American Chemical Society2009 131 (37), 13194-13195Nickel-Catalyzed Cycloaddition of Salicylic Acid Ketals to Alkynes via Elimination of Ketones
Akihiro Ooguri, Kenichiro Nakai, Takuya Kurahashi and Seijiro MatsubaraJournal of the American Chemical Society2009 131 (37), 13194-13195An intermolecular nickel-catalyzed addition reaction has been developed where salicylic acid ketals react with alkynes to afford substituted chromones. A mechanistic rationale is proposed, implying β-elimination of ketone from ring strained seven-membered ...
Mild Protocol for the Synthesis of Stable Nickel Complexes Having Primary and Secondary Silyl Ligands
Debashis Adhikari, Maren Pink and Daniel J. MindiolaOrganometallics2009 28 (7), 2072-2077Mild Protocol for the Synthesis of Stable Nickel Complexes Having Primary and Secondary Silyl Ligands
Debashis Adhikari, Maren Pink and Daniel J. MindiolaOrganometallics2009 28 (7), 2072-2077A mild protocol for the synthesis of (PNP)Ni(SiH2Ph) and (PNP)Ni(SiHPh2) (PNP− = N[2-P(CHMe2)2-4-MeC6H3]2) stemming from the hydride (PNP)NiH and silane in the presence of an activator is presented and discussed. A combination of preliminary reactivity ...
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History
- Published In Issue July 02, 2008
- Article ASAPJune 07, 2008
- Received: April 17, 2008
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