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六氟异丙醇作为 Passerini 反应中的酸性成分：一锅法制备β-氨基醇。

Hexafluoroisopropanol as the Acid Component in the Passerini Reaction: One-Pot Access to β-Amino Alcohols.

机构信息

Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines & Systems (AIMMS) , Vrije Universiteit Amsterdam , De Boelelaan 1108 , 1081 HZ Amsterdam , The Netherlands.

出版信息

Org Lett. 2018 Jul 6;20(13):3988-3991. doi: 10.1021/acs.orglett.8b01561. Epub 2018 Jun 15.

DOI:10.1021/acs.orglett.8b01561
PMID:29906122
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6038100/
Abstract

A new Passerini-type reaction in which hexafluoroisopropanol functions as the acid component is reported. The reaction tolerates a broad range of isocyanides and aldehydes, and the formed imidates can be reduced toward β-amino alcohols under mild and metal-free conditions. In addition, the imidate products were shown to undergo an unprecedented retro-Passerini-type reaction under microwave conditions, providing valuable mechanistic information about the Passerini reaction and its variations.

摘要

本文报道了一种新型的 Passerini 型反应，其中六氟异丙醇作为酸组分。该反应能容忍广泛的异氰化物和醛，形成的异氰酸酯在温和且无金属条件下可还原为β-氨基醇。此外，异氰酸酯产物在微波条件下还经历了前所未有的反 Passerini 型反应，为 Passerini 反应及其变化提供了有价值的机理信息。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/128f304f0f31/ol-2018-01561u_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/08ed80d190aa/ol-2018-01561u_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/2ebc38e525eb/ol-2018-01561u_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/2b0d195d22e2/ol-2018-01561u_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/6f06aad1dd7e/ol-2018-01561u_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/128f304f0f31/ol-2018-01561u_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/08ed80d190aa/ol-2018-01561u_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/2ebc38e525eb/ol-2018-01561u_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/2b0d195d22e2/ol-2018-01561u_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/6f06aad1dd7e/ol-2018-01561u_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a404/6038100/128f304f0f31/ol-2018-01561u_0005.jpg

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