Asymmetric Transfer Hydrogenation of α, β-Acetylenic Ketones

Matsumura, K.; Hashiguchi, Shohei; Ikariya, Takao; Noyori, Ryoji

doi:10.1021/ja971570a

Cited by 691 publications

(351 citation statements)

References 26 publications

(16 reference statements)

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“…[1] The transition-metal-based enantioselective hydrogenation or transfer hydrogenation of ketones in organic solvents [2][3][4][5][6][7][8][9][10] as well as in aqueous solutions [11][12][13][14][15][16][17][18][19][20][21] is one of the most commonly used synthetic approaches. Biotransformations of organic substrates by various enzymes have also found widespread applications, particularly because of their capability to efficiently perform enantioselective transformations.…”

Section: Introductionmentioning

confidence: 99%

Water‐Soluble Phenanthroline Complexes of Rhodium, Iridium and Ruthenium for the Regeneration of NADH in the Enzymatic Reduction of Ketones

2007

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Section: Introductionmentioning

confidence: 99%

Water‐Soluble Phenanthroline Complexes of Rhodium, Iridium and Ruthenium for the Regeneration of NADH in the Enzymatic Reduction of Ketones

2007

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“…To overcome this, we employed a chirality transfer from an allenylsilane. [22][23][24][25] Requisite allenylsilane 19 was prepared in an optically active form via an asymmetric reduction of a ketone under Noyori transfer hydrogenation conditions [26][27][28][29] and an S N 2′ reaction with a Lipshutz reagent. 30) Treatment of allenylsilane 19 with paraformaldehyde in the presence of TiCl 4 ·2THF afforded homopropargyl alcohol 20 in 52% yield.…”

Section: -21)mentioning

confidence: 99%

Synthesis of Natural Products with Polycyclic Systems

Yokoshima

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Herein we present our unique strategies to synthesize natural products. To prepare mersicarpine, an atypical indole alkaloid, our procedure features an Eschenmoser-Tanabe fragmentation to synthesize an alkyne unit, a combination of a Sonogashira coupling and a gold(III) catalyzed cyclization to construct the indole skeleton, and a one-pot process to arrange the cyclic imine and the hemiaminal moieties. Additionally, we synthesized a frog poison, histrionicotoxin, via a chirality transfer from an allenylsilane to prepare a pseudosymmetrical dienyne, dienyne metathesis to produce an optically active bicyclo [5.4.0] system, and an asymmetric propargylation. To synthesize lyconadin A, a Lycopodium alkaloid, a combination of an azaPrins reaction and electrocyclic ring opening constructed the highly fused tetracyclic compound. The synthesis of isoschizogamine features a facile construction of the carbon framework through a Wagner-Meerwein rearrangement, a tandem metathesis, a stereoselective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether.

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“…тиленового кетона 38: асимметрического гидридного восстановления по Нойори [23] до пропаргилового спир-та 39 и селективного переведения его в Е-алкен 40 (Схема 11).…”

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