A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-d-arabinitol using Co(III)(salen)-catalyzed hydrolytic kinetic resolution of a two-stereocentered anti-azido epoxide

Reddi, Rambabu N.; Prasad, Pragati K.; Kalshetti, Rupali G.; Sudalai, Arumugam

doi:10.1016/j.tetasy.2016.10.013

Cited by 7 publications

(3 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hydrolytic, phenolytic and alcoholytic ring-openings of terminal epoxides catalyzed with an oligomeric salen cobalt complex [19]. by 1 mol% of the same catalyst 1 [16]. This provided the corresponding almost enantiopure azido diol 5 in 50% yield which was further converted into expected DAB-1 through five supplementary steps in 18% overall yield.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Recent developments in enantioselective cobalt-catalyzed transformations

Pellissier

2018

Coordination Chemistry Reviews

View full text Add to dashboard Cite

Scheme 4. Hydrolytic and carbamolytic desymmetrizations of meso-epoxides catalyzed with an oligomeric salen cobalt complex [19]. Scheme 5. Hydrolytic ring-opening of epibromohydrin catalyzed with a tetrameric calix-salen cobalt complex [20]. Scheme 6. Hydrolytic ring-opening of epibromohydrin catalyzed with a combination of oligomeric calix-salen cobalt and manganese catalysts [21]. Scheme 7. Hydrolytic kinetic resolution of terminal epoxides catalyzed with a dinuclear salen cobalt complex incorporating Y(OTf) 3 [22]. Scheme 8. Hydrolytic kinetic resolution of terminal epoxides catalyzed with a macroporous helical silica-supported salen cobalt complex [23]. Scheme 12. Michael addition of malonates to cyclic a,b-unsaturated ketones [33]. Scheme 13. Michael addition of b-ketoamides to alkynones [34]. Scheme 16. Michael addition of amines to nitroolefins [36]. Scheme 17. Michael addition of dimethyl malonate to nitroolefins [37]. Scheme 20. Hydrogenations of exo-and endocyclic alkenes [41]. Scheme 21. Hydrogenation of 1,1-diarylethenes[42]. Scheme 24. Hydroboration of 1,1-disubstituted aryl alkyl alkenes [46]. Scheme 25. Hydroboration of 1,1-disubstituted aryl alkyl alkenes [47]. Scheme 26. Hydroboration of a-silyl alkenes [48]. Scheme 28. Hydroboration of aryl ketones [53]. Scheme 29. Hydrosilylation of aryl ketones [56]. Scheme 30. Hydrosilylation of alkenes [57]. Scheme 65. Darzens reaction of isatins with phenacyl bromides [118]. Scheme 66. Pauson-Khand reaction of norbornadiene with terminal alkynes [119].

show abstract

Section: Introductionmentioning

confidence: 99%

“…Efforts to develop novel asymmetric transformations have focused for a long time on the use of metals, including palladium, rhodium, copper, irid-Scheme 1. Hydrolytic kinetic resolutions of azido epoxides catalyzed with a salen cobalt complex and total syntheses of (+)-L-733,060 and DAB-1 [15,16]. ium and ruthenium.…”

Section: Introductionmentioning

confidence: 99%

Recent developments in enantioselective cobalt-catalyzed transformations

Pellissier

2018

Coordination Chemistry Reviews

View full text Add to dashboard Cite

show abstract

“…As a result, DAB-1 and nectrisine have been the targets of many synthetic efforts and remain useful targets to demonstrate stereoselective reaction methods in complex settings. A majority of these approaches utilized the chiral pool to establish many of the stereocenters; − however, a small subset of more recent syntheses has used other enantioselective methods to install the requisite stereochemistry. − As for our own approach, we envisioned the rapid, highly stereocontrolled syntheses of these molecules that would diverge from a single enantiopure precursor. More precisely, we would blend the utility of a highly enantioselective enzymatic reaction with the specificity of modern transition metal-catalyzed reactions to achieve this goal.…”

Section: Introductionmentioning

confidence: 99%

Combined Enzyme- and Transition Metal-Catalyzed Strategy for the Enantioselective Syntheses of Nitrogen Heterocycles: (−)-Coniine, DAB-1, and Nectrisine

et al. 2020

View full text Add to dashboard Cite

The enantioselective syntheses of (−)-coniine, DAB-1, and nectrisine have been developed, utilizing a complementary strategy of enzyme- and transition metal-catalyzed reactions. The initial stereocenter was set with >99% enantioselectivity via an enzyme-catalyzed hydrocyanation reaction. Substrate incompatibilities with the natural enzyme were overcome by tactical utilization of ruthenium-catalyzed olefin metathesis to functionalize an enzyme-derived (R)-allylic fragment. The piperidine and pyrrolidine alkaloid natural products were obtained by a route that leveraged regio- and stereoselective palladium-catalyzed 1,3-substitutive reactions.

show abstract

Enantioselective Cobalt‐Catalysed Transformations

Pellissier

2019

Cobalt Catalysis in Organic Synthesis

View full text Add to dashboard Cite

A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-d-arabinitol using Co(III)(salen)-catalyzed hydrolytic kinetic resolution of a two-stereocentered anti-azido epoxide

Cited by 7 publications

References 24 publications

Recent developments in enantioselective cobalt-catalyzed transformations

Recent developments in enantioselective cobalt-catalyzed transformations

Combined Enzyme- and Transition Metal-Catalyzed Strategy for the Enantioselective Syntheses of Nitrogen Heterocycles: (−)-Coniine, DAB-1, and Nectrisine

Enantioselective Cobalt‐Catalysed Transformations

Contact Info

Product

Resources

About