東華大學圖書館 |

Language: English

Help

回圖書館首頁

手機版館藏查詢

Back

Switch To: Labeled | MARC Mode | ISBD

Enantioselective Synthesis of Tertia...

Zhang, Xuntong Charlie,

Linked to FindBook

Google Book

Amazon

博客來

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

Record Type:	Electronic resources : Monograph/item
Title/Author:	Enantioselective Synthesis of Tertiary Boronic Esters Through Conjunctive Cross-Coupling and Cyclobutene Diboration // Xuntong Charlie Zhang.
Author:	Zhang, Xuntong Charlie,
Description:	1 electronic resource (739 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 85-07, Section: B.
Contained By:	Dissertations Abstracts International85-07B.
Subject:	Organic chemistry. -
Online resource:	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 /
LDR:03352nmm a22004333i 4500 001 2432349
005 20250707081445.5
006 m o d
007 cr|nu||||||||
008 261011s2024 miu||||||m |||||||eng d
020 $a 9798381445718
035 $a (MiAaPQD)AAI30990175
035 $a AAI30990175
040 $a MiAaPQD $b eng $c MiAaPQD $e rda
100 1 $a Zhang, Xuntong Charlie, $e author. $0 (orcid)0000-0003-0949-2198 $3 3821530
245 1 0 $a Enantioselective Synthesis of Tertiary Boronic Esters Through Conjunctive Cross-Coupling and Cyclobutene Diboration / $c Xuntong Charlie Zhang.
264 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2024
300 $a 1 electronic resource (739 pages)
336 $a text $b txt $2 rdacontent
337 $a computer $b c $2 rdamedia
338 $a online resource $b cr $2 rdacarrier
500 $a Source: Dissertations Abstracts International, Volume: 85-07, Section: B.
500 $a Advisors: Snapper, Marc M.; Morken, James J. Committee members: Zhang, Peter P.
502 $b Ph.D. $c Boston College $d 2024.
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.
546 $a English
590 $a School code: 0016
650 4 $a Organic chemistry. $3 523952
650 4 $a Chemistry. $3 516420
650 4 $a Materials science. $3 543314
653 $a Diboration reaction
653 $a Enantioselective dynthesis
653 $a Tertiary boronic esters
653 $a Transition metal catalysis
690 $a 0490
690 $a 0794
690 $a 0485
710 2 $a Boston College. $b GSAS - Chemistry. $e degree granting institution. $3 3821531
720 1 $a Snapper, Marc M. $e degree supervisor.
720 1 $a Morken, James J. $e degree supervisor.
773 0 $t Dissertations Abstracts International $g 85-07B.
790 $a 0016
791 $a Ph.D.
792 $a 2024
856 4 0 $u https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30990175