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2022 Fiscal Year Final Research Report

Development of novel Horner-Wadsworth-Emmons type reagents with phosphorus-sulfur single bonds

Research Project

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Project/Area Number 20K06966
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionThe University of Tokushima

Principal Investigator

SANO Shigeki  徳島大学, 大学院医歯薬学研究部(薬学域), 教授 (20226038)

Co-Investigator(Kenkyū-buntansha) 中尾 允泰  徳島大学, 大学院医歯薬学研究部(薬学域), 講師 (60550001)
Project Period (FY) 2020-04-01 – 2023-03-31
KeywordsHWE試薬 / 立体選択的反応 / リン原子 / 硫黄原子 / α,β-不飽和エステル / アレニルエステル / オレフィン化 / 不斉合成
Outline of Final Research Achievements

Methyl 2-[bis(benzylthio)phosphoryl]acetate, which was synthesized as a novel Horner-Wadsworth-Emmons (HWE) type reagent, found to afford allenyl esters in excellent yields in HWE type reaction and to exhibit remarkable E/Z selectivity dependent on the presence or absence of water in HWE type reactions with benzaldehyde. Furthermore, enantioselective HWE-type reactions of optically active HWE-type reagents bearing 1,3,2-thiazaphosphinane moieties with ketene were also successfully carried out.

Free Research Field

有機化学、分子創薬化学

Academic Significance and Societal Importance of the Research Achievements

新たに合成開発したホーナー・ワズワース・エモンズ型試薬(HWE型試薬)とアルデヒドあるいはケテンとのHWE型反応における特徴的なE/Z選択性や反応性は、HWE型試薬での第3周期元素同士の単結合(リン原子-硫黄原子単結合)の重要性を提起する初めての研究成果であり、既存のHWE試薬を凌駕する新たなHWE型試薬の開発へとつながる重要な知見を含んでいることから学術的意義は大きい。

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Published: 2024-01-30  

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