2,6-Bis(trifluoromethyl)phenylboronic Esters as Protective Groups for Diols: A Protection/Deprotection Protocol for Use under Mild Conditions

2,6-Bis(trifluoromethyl)phenylboronic Esters as Protective Groups for Diols: A Protection/Deprotection Protocol for Use under Mild Conditions

The application of 2,6-bis­(trifluoromethyl)­phenyl boronic acid (o-FXylB­(OH)2; o-FXyl = 2,6-(CF3)2C6H3) as a recoverable and reusable protective agent for diols is described. The resulting cyclic boronic esters are water- and air-stable and tolerant to various organic transformations. Moreover, th...

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Veröffentlicht in:Organic letters 2018-10, Vol.20 (19), p.6064-6068
Hauptverfasser: Shimada, Naoyuki, Urata, Sari, Fukuhara, Kenji, Tsuneda, Takao, Makino, Kazuishi
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container_end_page 6068
container_issue 19
container_start_page 6064
container_title Organic letters
container_volume 20
creator Shimada, Naoyuki
Urata, Sari
Fukuhara, Kenji
Tsuneda, Takao
Makino, Kazuishi
description The application of 2,6-bis­(trifluoromethyl)­phenyl boronic acid (o-FXylB­(OH)2; o-FXyl = 2,6-(CF3)2C6H3) as a recoverable and reusable protective agent for diols is described. The resulting cyclic boronic esters are water- and air-stable and tolerant to various organic transformations. Moreover, they can be deprotected under mild conditions. This methodology was applied to the synthesis of a highly conjugated enetriyne natural product with anti-angiogenic activities.
doi_str_mv 10.1021/acs.orglett.8b02427
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title 2,6-Bis(trifluoromethyl)phenylboronic Esters as Protective Groups for Diols: A Protection/Deprotection Protocol for Use under Mild Conditions
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