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Catalytic Enantioselective Synthesis of Secondary Organoboronates and Progress towards the Total Synthesis of Sarcodictyins.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Catalytic Enantioselective Synthesis of Secondary Organoboronates and Progress towards the Total Synthesis of Sarcodictyins./
Author:	Hu, Weipeng.
Description:	1 online resource (670 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 84-04, Section: B.
Contained By:	Dissertations Abstracts International84-04B.
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=29396362click for full text (PQDT)
ISBN:	9798351477398

Catalytic Enantioselective Synthesis of Secondary Organoboronates and Progress towards the Total Synthesis of Sarcodictyins.
Hu, Weipeng.

Catalytic Enantioselective Synthesis of Secondary Organoboronates and Progress towards the Total Synthesis of Sarcodictyins. - 1 online resource (670 pages)

Source: Dissertations Abstracts International, Volume: 84-04, Section: B.

Thesis (Ph.D.)--Boston College, 2022.

Includes bibliographical references

This dissertation will present three main projects focusing on the transition metal-catalyzed enantioselective synthesis of secondary organoboronic esters and progress towards the total synthesis of sarcodictyins. In the first project, a palladium-catalyzed enantioselective conjunctive cross-coupling reaction with propargylic electrophiles will be described. The tetra-substituted allenes are isolated with good yield and enantioselectivity and the beneficial effects of alcohol additives are investigated. The second project describes the enantioselective synthesis of α-boryl zinc reagents by a nickel-catalyzed carbozincation reaction. The in situ generated α-boryl zinc intermediate can be trapped by copper-mediated allylations, palladium-catalyzed Negishi cross-couplings, and cerium-mediated halogenation reactions to construct various chiral organoboranes. The synthetic utility of this methodology is showcased by the synthesis of natural products, including bruguierol A, (-)-aphanorphine, and (-)-enterolactone. The mechanism is studied with the assistance of EPR and deuterium-labeling experiments and a catalytic cycle through a Ni(I) intermediate is proposed. The third project depicts a synthetic route to essential precursors in the progress of the total synthesis of sarcodictyins. Various attempts to construct the ten-membered ring core of sarcodictyin have been made, including Sonogashira reaction, Dieckmann condensation, and lithium-halogen exchange process.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2023

Mode of access: World Wide Web

ISBN: 9798351477398Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

CatalysisIndex Terms--Genre/Form:

542853
Electronic books.

Catalytic Enantioselective Synthesis of Secondary Organoboronates and Progress towards the Total Synthesis of Sarcodictyins.
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504 $a Includes bibliographical references
520 $a This dissertation will present three main projects focusing on the transition metal-catalyzed enantioselective synthesis of secondary organoboronic esters and progress towards the total synthesis of sarcodictyins. In the first project, a palladium-catalyzed enantioselective conjunctive cross-coupling reaction with propargylic electrophiles will be described. The tetra-substituted allenes are isolated with good yield and enantioselectivity and the beneficial effects of alcohol additives are investigated. The second project describes the enantioselective synthesis of α-boryl zinc reagents by a nickel-catalyzed carbozincation reaction. The in situ generated α-boryl zinc intermediate can be trapped by copper-mediated allylations, palladium-catalyzed Negishi cross-couplings, and cerium-mediated halogenation reactions to construct various chiral organoboranes. The synthetic utility of this methodology is showcased by the synthesis of natural products, including bruguierol A, (-)-aphanorphine, and (-)-enterolactone. The mechanism is studied with the assistance of EPR and deuterium-labeling experiments and a catalytic cycle through a Ni(I) intermediate is proposed. The third project depicts a synthetic route to essential precursors in the progress of the total synthesis of sarcodictyins. Various attempts to construct the ten-membered ring core of sarcodictyin have been made, including Sonogashira reaction, Dieckmann condensation, and lithium-halogen exchange process.
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