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Enantioselective Synthesis of Tertia...

Zhang, Xuntong Charlie,

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Enantioselective Synthesis of Tertiary Boronic Esters Through Conjunctive Cross-Coupling and Cyclobutene Diboration /

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Enantioselective Synthesis of Tertiary Boronic Esters Through Conjunctive Cross-Coupling and Cyclobutene Diboration // Xuntong Charlie Zhang.
作者:	Zhang, Xuntong Charlie,
面頁冊數:	1 electronic resource (739 pages)
附註:	Source: Dissertations Abstracts International, Volume: 85-07, Section: B.
Contained By:	Dissertations Abstracts International85-07B.
標題:	Organic chemistry. -
電子資源:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30990175
ISBN:	9798381445718

Enantioselective Synthesis of Tertiary Boronic Esters Through Conjunctive Cross-Coupling and Cyclobutene Diboration /
Zhang, Xuntong Charlie,

Enantioselective Synthesis of Tertiary Boronic Esters Through Conjunctive Cross-Coupling and Cyclobutene Diboration /Xuntong Charlie Zhang. - 1 electronic resource (739 pages)

Source: Dissertations Abstracts International, Volume: 85-07, Section: B.

This dissertation will present three main projects focusing on the catalytic enantioselective synthesis and stereospecific functionalization of tertiary alkylboronates. In the first project, acyl chlorides were incorporated as a new class of electrophile in conjunctive crosscoupling, from which, a variety of tertiary β-boryl amides were successfully synthesized with high enantioselectivity. The utility of the tertiary alkylboronates products was also demonstrated through several orthogonal functionalizations of the boronic ester group and amide groups. The project culminated in the enantioselective total synthesis of natural product (+)-Adalinine that leveraged this newly developed methodology. In the second project, a conjunctive cross-coupling enabled ring closure was developed to synthesize tertiary alkylboronates residing on carbocyclic and heterocyclic scaffolds. A Phosphinooxazoline (Phox) ligand was identified as a non-expensive ligand that catalyzed the conjunctive cyclization reaction with high enantioselectivity. A Series of synthetically challenging enantimerically enriched spirocyclic and aryl bicyclic tertiary alkylboronates were efficiently generated using this method, and several cyclopentyl boronic esters with two continuous stereogenic centers were synthesized with high diastereoselectivity. In the third project, a Rh-catalyzed diboration reaction was successfully employed to diborate monosubstituted cyclobutenes with excellent enantioselectivity. The less sterically hindered secondary boronic ester units in the diboron products can be regioselectively functionalized using the newly developed tert-butyllithium activation-transmetallation strategy. As a result, a variety of stereochemically defined β-substituted cyclobutyl tertiary boronic esters were synthesized with high efficiency.

English

ISBN: 9798381445718Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

Diboration reaction

Enantioselective Synthesis of Tertiary Boronic Esters Through Conjunctive Cross-Coupling and Cyclobutene Diboration /
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520 $a This dissertation will present three main projects focusing on the catalytic enantioselective synthesis and stereospecific functionalization of tertiary alkylboronates. In the first project, acyl chlorides were incorporated as a new class of electrophile in conjunctive crosscoupling, from which, a variety of tertiary β-boryl amides were successfully synthesized with high enantioselectivity. The utility of the tertiary alkylboronates products was also demonstrated through several orthogonal functionalizations of the boronic ester group and amide groups. The project culminated in the enantioselective total synthesis of natural product (+)-Adalinine that leveraged this newly developed methodology. In the second project, a conjunctive cross-coupling enabled ring closure was developed to synthesize tertiary alkylboronates residing on carbocyclic and heterocyclic scaffolds. A Phosphinooxazoline (Phox) ligand was identified as a non-expensive ligand that catalyzed the conjunctive cyclization reaction with high enantioselectivity. A Series of synthetically challenging enantimerically enriched spirocyclic and aryl bicyclic tertiary alkylboronates were efficiently generated using this method, and several cyclopentyl boronic esters with two continuous stereogenic centers were synthesized with high diastereoselectivity. In the third project, a Rh-catalyzed diboration reaction was successfully employed to diborate monosubstituted cyclobutenes with excellent enantioselectivity. The less sterically hindered secondary boronic ester units in the diboron products can be regioselectively functionalized using the newly developed tert-butyllithium activation-transmetallation strategy. As a result, a variety of stereochemically defined β-substituted cyclobutyl tertiary boronic esters were synthesized with high efficiency.
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