Organocatalyzed Tsuji–Trost reaction: a new method for the closure of five- and six-membered rings

Vulovic, Bojan; Bihelovic, Filip; Matović, Radomir; Saičić, Radomir N.

doi:10.1016/j.tet.2009.10.006

Cited by 66 publications

(21 citation statements)

References 48 publications

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“…Oxidative cleavage of isopulegol with Pb(OAc) 4 produced aldehyde 121 which could be reclosed to 122 via palladium-catalyzed allylic alkylation of an in-situ formed enamine. 157 A significant quantity of C-2 epi - 122 was also produced in this reaction. A Reformatzky reaction between aldehyde 122 and α-bromoester 123 furnished 124 as an inconsequential mixture of diastereomers.…”

Section: Syntheses From the 21st Centurymentioning

confidence: 88%

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

et al. 2017

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The pool of abundant chiral terpene building blocks (i.e. “chiral pool terpenes”) has long served as a starting point for the chemical synthesis of complex natural products, including many terpenes themselves. As inexpensive and versatile starting materials, such compounds continue to influence modern synthetic chemistry. This review highlights 21st century terpene total syntheses which themselves use small, terpene-derived materials as building blocks. An outlook to the future of research in this area is highlighted as well.

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Section: Syntheses From the 21st Centurymentioning

confidence: 88%

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

et al. 2017

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“…An organocatalyzed variant was performed starting from malonate derivative bearing an aldehyde and allylic phosphonate group (eq 68). 93 The best results were obtained in the presence of MeOBIPHEP which allowed the efficient synthesis of a vinylcyclopentane with 98% ee. ( Intermolecular Pd-catalyzed Amination.…”

Section: Asymmetric Allylic Alkylation Amination and Mizoroki-heck-mentioning

confidence: 99%

(R)- and (S)-2,2′-Bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl

Schmid

Michelet

Scalone

et al. 2016

Encyclopedia of Reagents for Organic Synthesis

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“…De allí que estas reacciones sean ampliamente empleadas en la industria; se conocen como reacciones de acoplamiento y los trabajos pioneros corresponden a Tsuji y Trost [18] Las reacciones son catalizadas por complejos de Paladio y generalmente involucran la reducción inicial del Pd(II) a Pd(0), seguida por una adición oxidativa del R-X para generar un intermediario R-Pd(II), en donde R corresponde a un grupo alquilo. Entre ellas se resaltan: 1) Reacción Tsuji-Trost.…”

Section: Reacciones De Acoplamiento [17]unclassified

Catalizadores Organometálicos en la Industria Química

Sanabria

Pérez

2015

Publ. investig.

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resumenLos procesos catalíticos son cada vez más importantes en la industria. Gran número de productos quími-cos incluyen dentro de su producción reacciones catalizadas. La catálisis se entiende como un proceso por el cual se aumenta la velocidad de una reacción química, debido a la participación de una especie química denominada catalizador. El presente trabajo recopila cinco procesos industriales en los cuales son empleados catalizadores organometálicos en fase homogénea. Busca resaltar la importancia que tienen los complejos organometálicos como catalizadores, para la industria de química fina y farmacéutica. Se detallan aspectos mecanísticos en los que se puede ver el papel del centro metálico en las propiedades catalíticas del sistema, así como en la estructura del producto final.

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Organocatalyzed Tsuji–Trost reaction: a new method for the closure of five- and six-membered rings

Cited by 66 publications

References 48 publications

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

(R)- and (S)-2,2′-Bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl

Catalizadores Organometálicos en la Industria Química

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