Ni(II)-catalyzed Michael additions. Part 2: Dynamic kinetic resolution in the reduction of chiral α-hydrazino-β-ketoacid derivatives

Marchi, Caroline; Trepat, Elisenda; Moreno‐Mañas, Marcial; Vallribera, Adelina; Molins, Elı́es

doi:10.1016/s0040-4020(02)00538-0

Cited by 22 publications

(11 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similar transformations of the N-acetoacetyl derivative of Evans oxazolidinone 110 resulted in the enantiopure syn-1,2-hydrazinoalcohol derivative 112 with opposite C-1 and C-2 configurations from those in 109[113,114] (Scheme 23).Reagents and conditions: (i): (iPr)2NH, nBuLi, THF, -78 °C to 0 °C, 30 min, then 99a,b, THF, -78 °C, 1 h, CbzN=NCbz, THF, 3 min, 87% (100a), 57% (100b). (ii): LiBH(sBu)3, THF, -78 °C, 4 h, 87% (101a), 79% (101b) or LiAlH4, THF, -78 °C, 1.5 h, 89% (102a), 83% (102b).…”

mentioning

confidence: 96%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

View full text Add to dashboard Cite

Hydrazinoalcohols are versatile di-or trifunctional compounds with wide-ranging possibilities for application in organic synthesis. Numerous methods have been devised for the preparation of this family of compounds in recent decades. This review discusses the main pathways for the synthesis of hydrazinoalcohol derivatives, including epoxide ring-openings and nucleophilic substitutions by hydrazines, addition reactions to hydroxyhydrazones, hydrazine additions to olefinic bonds, electrophilic C-and N-amination reactions, cycloadditions, reductions of N-nitroso aminoalcohols and some unique procedures. The latest developments in these fields, involving both conventional and enzymatic catalytic methods of synthetic organic chemistry, allow the highly regio-, stereo-and enantioselective preparation of hydrazinoalcohol derivatives.

show abstract

mentioning

confidence: 96%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

View full text Add to dashboard Cite

show abstract

“…5,19 The starting β-keto imide ( 16 ) 20 can be synthesized through acetylation of Meldrum’s acid ( 14 ), 21 followed by treatment with 2-oxazolidinone ( 15 ). 22 …”

Section: Resultsmentioning

confidence: 99%

Tandem chain extension–Mannich reaction: an approach to β-proline derivatives

et al. 2012

View full text Add to dashboard Cite

show abstract

“…There exist only a handful of examples of the molecular transition‐metal‐based bifunctional catalysts for the base‐free Michael addition reaction to compare the results of the bifunctional catalyst 1 – 15 with. The first and the foremost is a Ni(acac) 2 complex 16 21 followed by a Ni(salicylaldehydate) 2 catalyst 17 28,29 that upon further improvement resulted in a organic‐perfluorinated biphasic homogeneous catalyst 18 30 (Figure 3).…”

Section: 3 Base‐free Michael Addition Reactionmentioning

confidence: 99%

The Developing Concept of Bifunctional Catalysis with Transition Metal N‐Heterocyclic Carbene Complexes

Ramasamy

Ghosh

2016

Eur J Inorg Chem

View full text Add to dashboard Cite

Though N-heterocyclic carbenes (NHCs) have long become popular as ligands of choice in transition metal mediated homogeneous catalysis, their related utility in bifunctional catalysis remains surprisingly overlooked. Conceptually more challenging, the bifunctional catalysis requires synchronous activations of substrates at complementary active-sites of a carefully crafted catalyst architecture, and which has been success- (Brookhaven National Laboratory, 1998-2001 and Professor Guillermo C. Bazan (University of California, Santa Barbara, 2001 fully realized in a number of interesting NHC-based bifucntional catalysts in recent times. The microreview summarizes the latest developments of this emerging area of the NHC-based bifunctional catalysis by looking into the underlying commonality existing behind these catalytic transformations from a mechanistic perspective.

show abstract

Ni(II)-catalyzed Michael additions. Part 2: Dynamic kinetic resolution in the reduction of chiral α-hydrazino-β-ketoacid derivatives

Cited by 22 publications

References 23 publications

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Tandem chain extension–Mannich reaction: an approach to β-proline derivatives

The Developing Concept of Bifunctional Catalysis with Transition Metal N‐Heterocyclic Carbene Complexes

Contact Info

Product

Resources

About