2020年9月1日
Chiral Brønsted Acid Catalyzed Enantioconvergent Propargylic Substitution Reaction of Racemic Secondary Propargylic Alcohols with Thiols
Chemistry - A European Journal
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- 巻
- 26
- 号
- 49
- 開始ページ
- 11124
- 終了ページ
- 11128
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/chem.202001609
- 出版者・発行元
- Wiley
Despite the significant progress of the enantioselective reaction using chiral catalysts, the enantioselective nucleophilic substitution reaction at the chiral sp3-hybridized carbon atom of a racemic electrophile has not been largely explored. Herein, we report the enantioconvergent propargylic substitution reaction of racemic propargylic alcohols with thiols using chiral bis-phosphoric acid as the chiral Brønsted acid catalyst. The substitution products were formed in high yields with high enantioselectivities in most cases. The cation-stabilizing effect of the sulfur functional group introduced at the alkynyl terminus is the key to achieving the efficient enantioconvergent process, in which chiral information originating from not only the racemic stereogenic center but also the formed contact ion pair is completely eliminated from the present system.
- リンク情報
- ID情報
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- DOI : 10.1002/chem.202001609
- ISSN : 0947-6539
- eISSN : 1521-3765
- ORCIDのPut Code : 78031195
- PubMed ID : 32274831
- SCOPUS ID : 85088702389