Catalytic Enantioselective Conjugate Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes

Ji, Jianguo; Barnes, David M.; Zhang, Ji; King, Steven A.; Wittenberger, Steven J.; Morton, Howard E.

doi:10.1021/ja992314w

Cited by 161 publications

(65 citation statements)

References 13 publications

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“…Scheme 40 In order to obtain highly functionalized derivatives, enantioselective catalytic conjugate additions of oxo esters and malonates to nitroalkenes have been developed. The first example was reported by Barnes et al, [66] who made use of bis(oxazoline) ligand 121 in the presence of Mg(OTf) 2 . This reaction is catalytic in ligandϪmetal complex and employs an amine cocatalyst.…”

Section: Asymmetric Michael Additions To Nitroalkenes Employing Enantmentioning

confidence: 99%

Asymmetric Michael Additions to Nitroalkenes

2002

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The asymmetric conjugate addition of various carbon and heteroatom nucleophiles to nitroalkenes as a tool for the construction of highly functionalized synthetic building blocks is presented. Diastereoselective, substrate-controlled 1,4-additions are also included. Besides auxiliary controlled asymmetric Michael additions, external asymmetric versions employing enantiopure additives, addition-elimination processes with enantiopure leaving groups, and catalytic asym-

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Section: Asymmetric Michael Additions To Nitroalkenes Employing Enantmentioning

confidence: 99%

Asymmetric Michael Additions to Nitroalkenes

2002

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“…Nitroalkenes are also good substrates for the rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids. 20 Although some successful results have been achieved on the asymmetric addition to a,b-unsaturated carbonyl compounds, there have been very few reports on the asymmetric addition to 1-nitroalkenes, 21 in spite of the wide applicability of nitro compounds to organic transformations. 22 It was found that 1-nitroalkenes undergo the 1,4-addition of boronic acids by the rhodium catalysis and the asymmetric reaction of 1-nitrocyclohexene (18) proceeds with high enantioselectivity and with high diastereoselectivity giving thermodynamically less stable cis isomer preferentially (Scheme 16).…”

Section: Scheme 13mentioning

confidence: 99%

Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids and Their Derivatives to Electron Deficient Olefins

Hayashi

2001

Synlett

259

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Asymmetric 1,4-arylation and -alkenylation was achieved by use of organoboronic acids or their derivatives in the presence of a rhodium catalyst coordinated with binap ligand. The reaction conditions are unique in that it is usually carried out in an aqueous solvent at 100°C. The scope of this asymmetric addition is very broad, a,b-unsaturated ketones, esters, 1-alkenylphosphonates, and 1-nitroalkenes being efficiently converted into the corresponding optically active 1,4-addition products with over 95% enantioselectivity. The catalytic cycle is proposed to involve the enantioselective addition of aryl-or alkenyl-rhodium intermediate to carbon-carbon double bond of the electron deficient olefins as a key step.

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“…Readily enolizable compounds such as β -ketoesters react with nitroalkenes in the presence of catalytic amounts of chiral bisoxazoline -magnesium trifl ate complex and N -methylmorpholine (NMM) as co -catalyst (Scheme 3.42 ) [81] .…”

Section: Pyrrolidinesmentioning

confidence: 99%