Palladium(II)-catalyzed 1,4-addition of arylboronic acids to β-arylenals for enantioselective syntheses of 3,3-diarylalkanals: a short synthesis of (+)-(R)-CDP 840

Nishikata, Takashi; Yamamoto, Yasunori; Miyaura, Norio

doi:10.1016/j.tetlet.2007.04.038

Cited by 59 publications

(25 citation statements)

References 39 publications

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“…When the methodology was extended to β-aryl enals (31), it was again found that the addition of HBF 4 and AgBF 4 caused a dramatic increase in the reaction rate. It was proposed that an additional role of HBF 4 was to accelerate the rate of exchange between aldehyde and their corresponding hydrates, which is their favored form in aqueous solvents (Scheme 1.83) [248]. Minnaard and coworkers reported that the Pd-catalyzed ECA is efficiently catalyzed by Pd(OCOCF 3 ) 2 as a catalyst precursor [249].…”

Section: Pd-catalyzed Eca 59mentioning

confidence: 99%

Rhodium‐ and Palladium‐Catalyzed Asymmetric Conjugate Additions

Berthon

Hayashi

2010

Catalytic Asymmetric Conjugate Reactions

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Section: Pd-catalyzed Eca 59mentioning

confidence: 99%

Rhodium‐ and Palladium‐Catalyzed Asymmetric Conjugate Additions

Berthon

Hayashi

2010

Catalytic Asymmetric Conjugate Reactions

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“…For the corresponding palladium-catalyzed reactions of organoboron, -silicon, and -bismuth compounds, bisphosphines bridged by two carbons, such as chiraphos (116) and dipamp (117), result in high yields and high enantioselectivities. 75,[107][108][109][110][111][112][113][114][115][116] Performance of these chiral ligands for enantioselectivities is shown in Scheme 18. The binap ligand 115 achieves high enantioselectivities for both cyclic and acyclic substrates.…”

Section: Gmentioning

confidence: 99%

Metal-Catalyzed Reactions of Organoboronic Acids and Esters

Miyaura¹

2008

Bulletin of the Chemical Society of Japan

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365

110

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Metal-catalyzed B-C and C-C bond-forming reactions of organoboronic acids that have been pursued in the past three decades by our group are summarized in this article. B-C bond-forming reactions for the synthesis of organoboronic acid derivatives include metal-catalyzed addition reactions of pinacolborane or catecholborane (hydroboration), bis(pinacolato)diboron (diboration), and alkylthioboranes (thioboration) to alkenes, alkynes, 1,3-alkadienes, or 1,2-alkadienes (allenes). Other B-C bond-forming reactions include coupling reactions of pinacolborane or bis(pinacolato)diboron for borylation of C-halogen bonds with palladium catalysts and C-H bonds of arenes and alkenes with iridium catalysts. These reactions have provided a convenient new access to aryl-, 1-alkenyl-, allyl-, or benzylboronates. Metal-catalyzed C-C and C-N bond-forming reactions using boronic acid derivatives include synthesis of novel cyclic triolborate salts for palladium-or copper-catalyzed cross-coupling reactions with organic halides or amines, rhodium-or palladiumcatalyzed 1,4-addition reactions of arylboronic acids to ,-unsaturated carbonyl compounds and rhodium-catalyzed addition of aryl-and 1-alkenylboronic acids to aldehydes and imines.

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“…128,129 However, the applications of bis-sulfoxide ligands in stereoselective synthesis have been largely overlooked. [130][131][132][133][134][135][136][137] In 2008, Dorta et al have disclosed that chiral bis-sulfoxides can be employed as ligands in stereoselective late-transition metal catalysis. Pre-catalyst [{(P,R,R)-p-tol-BINASO}RhCl] 2 L24 acts as a reactive showing excellent stereoselectivities in the 1,4-addition of different arylboronic acids 2 to cyclic, electron-poor compounds 1a-c,g,w.…”

Section: Methodsmentioning

confidence: 99%

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Heravi

Dehghani

Zadsirjan

2016

Tetrahedron: Asymmetry

106

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Rh-catalyzed asymmetric 1,4-addition reactions to a,b-unsaturated carbonyl and related compounds: an update Available online xxxx Dedicated to my son, OMID on the occasion of his 35th birthday. a b s t r a c tThe Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to an appropriate receptor has been a growing area of research over the last decade. The receptors for such a 1,4-addition reaction are chiefly a,b-unsaturated ketones, esters, amides, enones, nitroalkenes, and occasionally phosphonates etc. This reaction in the presence of chiral rhodium complexes introduce the aryl and alkenyl groups at the b-position of the above electron poor olefins, enantioselectively. Chiral Rh complexes similar to other transition metals can be added to some electron poor olefins, in turn making them viable to attack by various organometallic reagents for highly enantioselective C-C bond formation. The Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to electron poor olefins has been reviewed in 2003. Due to the importance of the asymmetric C-C bond formation via 1,4-conjugate addition reactions and the number of such reactions catalyzed by Rh-complexes, in this review we highlight the recent advances in Rh-complex asymmetric catalyzed 1,4-addition reactions since 2003.

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Palladium(II)-catalyzed 1,4-addition of arylboronic acids to β-arylenals for enantioselective syntheses of 3,3-diarylalkanals: a short synthesis of (+)-(R)-CDP 840

Cited by 59 publications

References 39 publications

Rhodium‐ and Palladium‐Catalyzed Asymmetric Conjugate Additions

Rhodium‐ and Palladium‐Catalyzed Asymmetric Conjugate Additions

Metal-Catalyzed Reactions of Organoboronic Acids and Esters

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

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