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020 ▼a 9781687922595
035 ▼a (MiAaPQ)AAI22622194
040 ▼a MiAaPQ ▼c MiAaPQ ▼d 247004
0820 ▼a 540
1001 ▼a Sherbrook, Evan Michael.
24514 ▼a The Development of Stereoselective Photocycloadditions via Lewis and Bronsted Acid Catalysis.
260 ▼a [S.l.]: ▼b The University of Wisconsin - Madison., ▼c 2019.
260 1 ▼a Ann Arbor: ▼b ProQuest Dissertations & Theses, ▼c 2019.
300 ▼a 493 p.
500 ▼a Source: Dissertations Abstracts International, Volume: 81-04, Section: B.
500 ▼a Advisor: Yoon, Tehshik P.
5021 ▼a Thesis (Ph.D.)--The University of Wisconsin - Madison, 2019.
506 ▼a This item must not be sold to any third party vendors.
520 ▼a Stereoselective cycloadditions are highly regarded transformations for their ability to introduce both molecular complexity and asymmetry in a single step. As photocatalysis has become an increasingly valuable tool in organic synthesis, there has been significant interest in the development of enantioselective photochemical cycloaddition reactions. Despite this, there are few general approaches to the control of absolute stereochemistry of photocycloadditions. This thesis describes the use of chiral catalysts, including Lewis and Bronsted acids, to enable highly enantioselective photocycloadditions. Chiral Lewis acids were employed in conjunction with a ruthenium photocatalyst to facilitate the photoreductive ring opening of cyclopropyl ketones in a reaction with alkenes to generate enantioenriched cyclopentanes. Following this, protic acids were explored as catalysts for enabling the triplet sensitization of imidazoyl enones in [2+2] photocycloadditions with several types of olefins. Lastly, investigations of BINOL-derived phosphoramidates as chiral Bronsted acid catalysts have allowed for the stereoselective synthesis of cyclobutanes, surprisingly without the need for transition metal photocatalysts.
590 ▼a School code: 0262.
650 4 ▼a Organic chemistry.
650 4 ▼a Chemistry.
690 ▼a 0490
690 ▼a 0485
71020 ▼a The University of Wisconsin - Madison. ▼b Chemistry.
7730 ▼t Dissertations Abstracts International ▼g 81-04B.
773 ▼t Dissertation Abstract International
790 ▼a 0262
791 ▼a Ph.D.
792 ▼a 2019
793 ▼a English
85640 ▼u http://www.riss.kr/pdu/ddodLink.do?id=T15493880 ▼n KERIS ▼z 이 자료의 원문은 한국교육학술정보원에서 제공합니다.
980 ▼a 202002 ▼f 2020
990 ▼a ***1816162
991 ▼a E-BOOK