DAST-mediated ring-opening of cyclopropyl silyl ethers in nitriles: facile synthesis of allylic amides <i>via</i> a Ritter-type process-Reference-Cited by-同舟云学术

DAST-mediated ring-opening of cyclopropyl silyl ethers in nitriles: facile synthesis of allylic amides via a Ritter-type process

Published:2022 Issue:33 Volume:20 Page:6558-6561
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Kirihara Masayuki¹^ORCID,Nakamura Riho¹,Nakakura Kana¹,Tujimoto Kazuki¹,Salem Mohamed S. H.²³^ORCID,Suzuki Takeyuki²^ORCID,Takizawa Shinobu²^ORCID

Affiliation:

1. Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan

2. SANKEN, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan

3. Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt

Abstract

A diethylaminosulfur trifluoride (DAST)-mediated ring-opening reaction of cyclopropyl silyl ethers in nitriles produced allylic amides in moderate to good yields (up to 87%).

Funder

Ministry of Education, Culture, Sports, Science and Technology

Hoansha Foundation

Novartis Foundation

Artificial Intelligence Research Center

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/OB/D2OB00940D

Reference21 articles.

1. The Chemistry of Cyclopropanols

2. Total syntheses via cyclopropanols

3. Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

4. Allylic fluorides via the cleavage of tertiary cyclopropyl silyl ethers with diethlaminosulfur trifluoride

5. Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride: the effects of substituents on the cleavage of the cyclopropane ring

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1. Ritter-Type Reaction;Reference Module in Chemistry, Molecular Sciences and Chemical Engineering;2024

2. Isolation and Reactions of Imidoyl Fluorides Generated from Oxime Using the Diethylaminosulfur Trifluoride/Tetrahydrofuran (DAST–THF) System;Organic Letters;2023-05-09