Chiral (Acyloxy)borane Catalyzed Asymmetric Allylation of Aldehydes

Furuta, Kyoji; Mouri, Makoto; Yamamoto, Hisashi

doi:10.1055/s-1991-20797

Cited by 131 publications

(35 citation statements)

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“…50 The CAB catalyst 9 is prepared by mixing borane‚THF with mono(2,6-diisopropoxy)-benzoyltartaric acid. The structure of this complex is proposed to be a five-membered boronic ester.…”

Section: Chiral Acyloxy Borane (Cab)-catalyzed Allylation Reactionsmentioning

confidence: 99%

Catalytic Enantioselective Addition of Allylic Organometallic Reagents to Aldehydes and Ketones

2003

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“…50 The CAB catalyst 9 is prepared by mixing borane‚THF with mono(2,6-diisopropoxy)-benzoyltartaric acid. The structure of this complex is proposed to be a five-membered boronic ester.…”

Section: Chiral Acyloxy Borane (Cab)-catalyzed Allylation Reactionsmentioning

confidence: 99%

Catalytic Enantioselective Addition of Allylic Organometallic Reagents to Aldehydes and Ketones

2003

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“…This limitation is addressed, in part, by the groundbreaking work of Yamamoto [221] and subsequent studies by Umani-Ronchi [222] and Keck [223] on chiral Lewis acid catalysts for enantioselective carbonyl allylation. Chiral Lewis base-catalyzed enantioselective carbonyl allylations soon followed, as reported by Denmark [224].…”

Section: Iridium-catalyzed Hydrogenation For C–c Bond Formationmentioning

confidence: 99%

“… 20 For selected examples of catalytic asymmetric carbonyl allylation employing allylmetal reagents, see [221–224]. …”

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confidence: 99%

Formation of C–C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation

2010

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The formation of C-C bonds via catalytic hydrogenation and transfer hydrogenation enables carbonyl and imine addition in the absence of stoichiometric organometallic reagents. In this review, iridium-catalyzed C-C bond-forming hydrogenations and transfer hydrogenations are surveyed. These processes encompass selective, atom-economic methods for the vinylation and allylation of carbonyl compounds and imines. Notably, under transfer hydrogenation conditions, alcohol dehydrogenation drives reductive generation of organoiridium nucleophiles, enabling carbonyl addition from the aldehyde or alcohol oxidation level. In the latter case, hydrogen exchange between alcohols and π-unsaturated reactants generates electrophile-nucleophile pairs en route to products of hydro-hydroxyalkylation, representing a direct method for the functionalization of carbinol C-H bonds.

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“…Repetitive allylation of dialdehydes and bis(allylsilane)s in the presence of chiral catalysts produced optically active polymers having asymmetric carbons in the main chain [101,102] . Among the monomers ever examined, dialdehyde ( 54 ) and bis(allylsilane) ( 55 ) showed excellent reactivity toward asymmetric polymerization in the presence of chiral (acyloxy)borane ( 56 ) [103,104] to give the polymer ( 57 ) with high molecular weight (14,000) and a high molar optical rotation of [ Φ ] 405 +1144 ° [101] . The optical purity of 57 was estimated to be approximately 75% ee according to a model reaction between benzaldehyde and methallyltrimethylsilane although the exact enantiometric purity of the polymer is still unknown [101] .…”

Section: Allylation Polymerizationmentioning

confidence: 99%