Axially Chiral Phosphinamine Ligands in Asymmetric Catalysis

Guiry, Patrick J.; McCarthy, Marie; Lacey, Patrick M.; Saunders, Cormac P.; Kelly, Sarah; Connolly, David

doi:10.2174/1385272003376049

Cited by 38 publications

(17 citation statements)

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“…Addition of the B-H bond did occur at elevated temperatures but competing degradation of the borane made these reactions synthetically unattractive. With rhodium complexes being the most commonly used in catalyzed hydroborations, we decided to initiate our studies using 5 mol% RhCl(PPh 3 ) 3 . Unlike other diorganyloxyboranes, however, no reaction was observed with 1 and 1-octene using this catalyst precursor.…”

Section: Resultsmentioning

confidence: 99%

“…The discovery that certain transition metal complexes catalyze the addition of catecholborane (HBcat, cat = 1,2-O 2 C 6 H 4 ) or pinacolborane (HBpin, 1,2-O 2 C 2 Me 4 ) to unsaturated substrates has become an important strategy in organic synthesis [1][2][3][4][5][6][7][8]. Products obtained using a transition metal catalyzed hydroboration can have regio-, chemo-, or stereoselectivities complementary, or more remarkably, opposite to those from products obtained via the uncatalyzed route.…”

Section: Introductionmentioning

confidence: 99%

“…However, selective addition of HBcat to the less reactive alkene group was achieved if the reaction was carried out at lower temperatures in the presence of a rhodium catalyst, e.g. RhCl(PPh 3 ) 3 . Since this remarkable discovery, a considerable amount of research has focussed on investigating the mechanism and scope of catalyzed hydroboration reactions [6,[10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…hydrogenation and/or dehydrogenative borylations) to give several organoboronate ester products. As such, we have investigated the use of bulky 4,8-ditert-butyl-2,10-dimethyl-12H-dibenzo [d,g] [1,3,2]dioxaborocine (1, HBdd, where dd = 6,6 0 -methylenebis(2-tert-butyl-4-methylphenolato)) for its use in the catalyzed hydroboration of alkenes.…”

Section: Introductionmentioning

confidence: 99%

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[Cp*IrCl2]2 catalyzed hydroborations of alkenes using a bulky dioxaborocine

Hunter

Vogels

Decken

et al. 2011

Inorganica Chimica Acta

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

[Cp*IrCl2]2 catalyzed hydroborations of alkenes using a bulky dioxaborocine

Hunter

Vogels

Decken

et al. 2011

Inorganica Chimica Acta

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“…These ligands, as well as having the potential to induce asymmetry through steric factors, can also generate electronic asymmetry on the metal centre due to the combination of hard and soft donor atoms and the different reactivity associated with each. [107,108] Scheme 9.…”

Section: Chiral Pp Ligandsmentioning

confidence: 99%

The Development of Enantioselective Rhodium-Catalysed Hydroboration of Olefins

Carroll

O’Sullivan

Guiry

2005

Advanced Synthesis & Catalysis

333

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Rhodium-catalysed enantioselective hydroboration of olefins is a valuable synthetic transformation, typically employing a chiral catalyst and an achiral borane source. The pertinent chemo-, regio-and enantioselectivity issues of this reaction are discussed. However, the main emphasis of this review is on the evolution of catalytic asymmetric hydroboration. This has primarily relied upon the development and application of chiral bidentate P,P and P,N ligands which have exhibited varying degrees of success in this transformation.

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Hydroboration CatalysisBased in part on the article Hydroboration Catalysis by Kevin Burgess & Wilfred A. van der Donk which appeared in the Encyclopedia of Inorganic Chemistry, First Edition .

Vogels¹,

Westcott²

2005

Encyclopedia of Inorganic Chemistry

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Among the most significant advances in organic synthesis over the past few decades are those associated with the development of transition metal complexes for their use as catalysts in organic reactions. The discovery that transition metals can also be used to catalyze the addition of BH bonds to unsaturated substrates has provided the synthetic chemist with another valuable tool. This review examines recent advances in the field of catalyzed hydroborations and their applications in organic synthesis.

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Axially Chiral Phosphinamine Ligands in Asymmetric Catalysis

Cited by 38 publications

References 0 publications

[Cp*IrCl2]2 catalyzed hydroborations of alkenes using a bulky dioxaborocine

[Cp*IrCl2]2 catalyzed hydroborations of alkenes using a bulky dioxaborocine

The Development of Enantioselective Rhodium-Catalysed Hydroboration of Olefins

Hydroboration CatalysisBased in part on the article Hydroboration Catalysis by Kevin Burgess & Wilfred A. van der Donk which appeared in the Encyclopedia of Inorganic Chemistry, First Edition .

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