Catalytic Aerobic Oxidation of p-Methoxybenzyl (PMB) Ethers to Aldehydes or Ketones.

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Tác giả: Shengming Ma, Hui Qian, Qian Zhang

Ngôn ngữ: eng

Ký hiệu phân loại: 661.85 *Aldehydes and ketones

Thông tin xuất bản: Germany : Chemistry (Weinheim an der Bergstrasse, Germany) , 2025

Mô tả vật lý:

Bộ sưu tập: NCBI

ID: 168667

An efficient and highly selective aerobic oxidation of p-methoxybenzyl ethers to aldehydes or ketones with Fe(NO3)3•9H2O and TEMPO as catalysts at 25 oC has been developed. This method is compatible with versatile functional groups: adamantyl, ether, alkynyl, and alkenyl, etc. Due to the mild nature of the reaction conditions, even the highly sensitive optically active aldehydes with an easily racemized α-chiral center could be formed from optically active PMB ethers without racemization. Other protecting groups of hydroxyl group remained intact during the current aerobic oxidation. The catalytic protocol has been successfully applied to synthesis of (R)-tert-butyldimethylsilyl hept-1-en-6-yn-4-yl ether, which is the key intermediate for the total synthesis of natural product, (-)-6-O-methylcitreoisocoumarin.
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