Lewis Acid-Promoted Diastereoselective Cross-Coupling of Boronic Acids and Aryl-Substituted 1,2-Diols

Author(s)
유희선
Alternative Author(s)
Heesun Yu
Advisor
이동주
Department
일반대학원 약학과
Publisher
The Graduate School, Ajou University
Publication Year
2021-08
Language
eng
Keyword
9-norneolignanboronic acidcross couplingdiollewis acid
Abstract
A Lewis acid-promoted highly diastereoselective C(sp3)–C(sp2) cross-coupling reaction of aryl-substituted 1,2-diols and a variety of styryl, aryl, heteroaryl and polyaryl boronic acids as nucleophiles has been developed in a one-pot process under mild reaction conditions. The regioselective opening of aryl-substituted cyclic boronic esters promoted by a Brønsted or Lewis acid and subsequent intramolecular 1,4-transfer of the carbon ligand from boron atom to the same face of the resulting resonance-stabilized planar benzylic carbenium ion in a stereospecific fashion led to highly diastereoselective C–C bond formation at the benzylic carbon center. The synthetic value of this method has been demonstrated by a unified enantioselective total synthesis of 9-norneolignan natural products (–)-agatharesinol, (–)-agatharesinol acetonide, (–)-sugiresinol and (+)-hinokiresinol in 6 to 8 steps from the commercially available methyl 3-(4-hydroxyphenyl)acrylate.
URI
https://dspace.ajou.ac.kr/handle/2018.oak/20352
Fulltext

Appears in Collections:
Graduate School of Ajou University > Department of Pharmacy > 4. Theses(Ph.D)
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse