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020 ▼a 9781392484241
035 ▼a (MiAaPQ)AAI27543532
040 ▼a MiAaPQ ▼c MiAaPQ ▼d 247004
0820 ▼a 540
1001 ▼a Yan, Lu .
24510 ▼a Carbohydrate-catalyzed Enantioselective Alkene Diboration and Its Synthetic Application.
260 ▼a [S.l.]: ▼b Boston College., ▼c 2019.
260 1 ▼a Ann Arbor: ▼b ProQuest Dissertations & Theses, ▼c 2019.
300 ▼a 567 p.
500 ▼a Source: Dissertations Abstracts International, Volume: 81-06, Section: B.
500 ▼a Advisor: Snapper, Marc L.
5021 ▼a Thesis (Ph.D.)--Boston College, 2019.
506 ▼a This item must not be sold to any third party vendors.
520 ▼a Abstract: This dissertation will present four main projects that I have been working on since January 2015. The first two chapters will be focusing on the developments of the carbohydrate-catalyzed enantioselective alkene diboraiton. The exchange catalysis between carbohydrate-derived diol catalyst and diboron starting material renders the alkene diboration reaction possible without the aid from transition metals. This successfully brought down the cost for the enantioselective alkene diboration, making it an appealing tool for alkene transformation. Detailed mechanistic study that leads to the reaction efficiency improvements were discussed in chapter 2. The third chapter of this dissertation is about the developments of site-selective oxidation of 1,2-bis(boronate). This is a new type of a reaction motif that the alkene diboration product can undergo. The secondary boronic ester of the 1,2-bis(boronate) was selectively oxidized to hydroxyl group while leaving the primary boronic ester untouched. This new reaction opens up a variety of opportunities to transform 1,2-bis(boronate) into different functional groups. Lastly, in the fourth chapter, recent synthetic methods developed in the Morken group was used in the total synthesis study of complex natural product Amphidinolide C. As it is disclosed, the carbohydrate-catalyzed enantioselective alkene diboration proved to be a powerful transformation either in early stage starting material preparation or in late stage complex structure motif functionalization.
590 ▼a School code: 0016.
650 4 ▼a Chemistry.
690 ▼a 0485
71020 ▼a Boston College. ▼b GSAS - Chemistry.
7730 ▼t Dissertations Abstracts International ▼g 81-06B.
773 ▼t Dissertation Abstract International
790 ▼a 0016
791 ▼a Ph.D.
792 ▼a 2019
793 ▼a English
85640 ▼u http://www.riss.kr/pdu/ddodLink.do?id=T15494460 ▼n KERIS ▼z 이 자료의 원문은 한국교육학술정보원에서 제공합니다.
980 ▼a 202002 ▼f 2020
990 ▼a ***1008102
991 ▼a E-BOOK