The synthesis of (+)- and (−)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylarsino)butane and their use in asymmetric catalysis

Calhoun, Aubrey D.; KOBOS, W. J.; Nile, Terence A.; Smith, C. A.

doi:10.1016/s0022-328x(00)81081-5

Cited by 16 publications

(10 citation statements)

References 11 publications

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“…The rates are slower than with phosphine based catalysts (21,22) and the optical yields are low. The products also have the opposite configuration.…”

Section: Hydrogenation Studiesmentioning

confidence: 92%

Asymmetric homogeneous hydrogenation of olefins catalyzed by alkylphosphine complexes of rhodium(I)

Cullen¹,

Woollins²

1982

Can. J. Chem.

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The cationic rhodium(I) complexes of the optically active ferrocenes, C5H5FeC5H3[CH(CH3)N(CH3)2][ER2]-1,2, catalyze the asymmetric hydrogenation of acetamidoacrylic acid derivatives, itaconic acid and styrene, when ER2 is P(C6H5)2 or P(C(CH3)3)2. The configuration of the product is reversed on substituting C6H5 for C(CH3)3 groups. The catalyst with the tert-butyl groups can afford higher optical yields and is faster overall. The rhodium(I) complexes of the arsenic derivatives ER2 = As(C6H5)2 or As(CH3)2 do not catalyze the hydrogenation reactions. The nmr spectrum of the arsenic complex (ER2 = As(C6H5)2) is temperature dependent which seems to be due to a process involving the making and breaking of the Rh—N bond. The unsuccessful use of the MEM group (β-methoxyethoxymethyl) to protect an alcohol function α to a ferrocene ring is described. The hydrogenation results are discussed in the light of models which are currently used to predict the results of rhodium(I) catalyzed reactions but which are inapplicable to this work.

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“…The rates are slower than with phosphine based catalysts (21,22) and the optical yields are low. The products also have the opposite configuration.…”

Section: Hydrogenation Studiesmentioning

confidence: 92%

Asymmetric homogeneous hydrogenation of olefins catalyzed by alkylphosphine complexes of rhodium(I)

Cullen¹,

Woollins²

1982

Can. J. Chem.

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“…In contrast to their phosphine analogues, chiral arsines are less extensively studied due to the technical challenges encountered in their synthesis. Hence, their applications have been scarcely reported even to date [10][11][12][13]. Among the various types of chiral phosphines reported in the literatures, much interests are being focused on chiral diphosphines [2,[14][15][16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Asymmetric synthesis of a chiral arsinophosphine via a metal template promoted asymmetric Diels–Alder reaction between diphenylvinylphosphine and 2-furyldiphenylarsine

Tan¹,

Liu²,

Li³

et al. 2006

Journal of Organometallic Chemistry

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“…The chiral bidentate (R,R)-Diarsop 32 was synthesised by the reaction of 1,4-ditosyl-2,3-o-isoproplylidene-D-threitol with potassium diphenylarsenide dioxanate in THF and dioxane (Scheme 1.17). 25 The product was obtained as air-stable solid. mol and bis(1,5-cyclooctadine)nickel and 11 mol% bis(diphenylphosphino)ethane in DMF at 100 C for 3 days (Scheme 1.18).…”

Section: Preparation From Naturally Occurring Chiral Starting Materialsmentioning

confidence: 99%

Asymmetric ligand transformation reactions promoted by cyclometallated complexes

Cheow¹

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for sharing their technical skill with me. I would like to thank my laboratory mates Deepa, Yinhua, Xu Chang, Chen Ke, Zhang Na, Jeanette, Kim and Zhiyi for sharing the good and bad times with me. I am grateful to the staff Eeling and Shuqi for their assistance in NMR and elemental analysis and to Celine for her help with regards to graduate matters. I am grateful to Nanyang Technological University for the award of a research scholarship. Most importantly, to my parents, I would like to express my heartfelt gratitude for their love and support during the pursuit for my PhD degree.

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The synthesis of (+)- and (−)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylarsino)butane and their use in asymmetric catalysis

Cited by 16 publications

References 11 publications

Asymmetric homogeneous hydrogenation of olefins catalyzed by alkylphosphine complexes of rhodium(I)

Asymmetric homogeneous hydrogenation of olefins catalyzed by alkylphosphine complexes of rhodium(I)

Asymmetric synthesis of a chiral arsinophosphine via a metal template promoted asymmetric Diels–Alder reaction between diphenylvinylphosphine and 2-furyldiphenylarsine

Asymmetric ligand transformation reactions promoted by cyclometallated complexes

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