A mild and metal-free synthesis of chiral 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazines

Zhao, Hongshan; Li, Shengnan; Cheng, Shihao; Lin, Ziyun; Zhang, Dongfeng; Huang, Huanwei

doi:10.1016/j.tet.2021.132304

Cited by 3 publications

(1 citation statement)

References 18 publications

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“…The same research groups very recently reported KOH‐mediated conversion of enantio‐ and diastereomerically pure 2,3‐epoxy‐4‐trityloxybutanols ( 237 ) into 3‐hydroxymethyl‐1,4‐benzoxazines ( 238 ) in an enantio‐ and diastereospecific fashion (Scheme 57). [70] The cyclized products were obtained in 52 %‐94 % yields and 95 % to >99 % ee's. From a mechanistic point of view, the reactions occurred through a 6‐ exo carbamte‐epoxide cyclization, followed by a hydrolysis process of the carabamate moiety.…”

Section: Construction Of Benzo‐fused Heterocycles By Epoxide‐n‐nucleo...mentioning

confidence: 97%

Construction of Benzo‐Fused Heterocycles by Epoxide–Heteronucleophile Cyclization: Applications in the Synthesis of Natural Products and Designed Molecules

Das

2022

Eur J Org Chem

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Construction of benzo‐fused heterocycles, specifically which have one or more sp3 stereogenic carbon atoms on the heterocyclic ring, by intramolecular ring‐opening cyclization of epoxides with O‐ and N‐nucleophiles is a powerful synthetic tool in organic synthesis. In this Review, we analyze the efficiency of such a heterocyclization approach in natural product synthesis and synthetic methodologies published since the year 2000. In addition to briefly discussing the synthetic methods of accessing the requisite epoxide substrates, important aspects of the subsequent cyclization reaction, such as reaction conditions, endo‐ versus exo‐regioselectivity, protecting or functional group compatibility, and enantio‐ and distereoselectivity are surveyed. Although the literature of organic chemistry in the last four decades has witnessed a large number of reviews/book chapters on the epoxide ring‐opening chemistry, the title topic has never been reviewed. Herein, we have systematized it as a dedicated review for the first time.

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Section: Construction Of Benzo‐fused Heterocycles By Epoxide‐n‐nucleo...mentioning

confidence: 97%

Construction of Benzo‐Fused Heterocycles by Epoxide–Heteronucleophile Cyclization: Applications in the Synthesis of Natural Products and Designed Molecules

Das

2022

Eur J Org Chem

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Three-membered ring systems

Russel¹

2023

Progress in Heterocyclic Chemistry

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Tandem Amination/Oxetane Ring Opening toward Benzomorpholines

DeRatt

Kuduk

2021

J. Org. Chem.

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Herein, a tandem approach that allows rapid access to the benzomorpholine scaffold is reported. This operationally simple method allows for valuable heterocycles to be isolated in moderate to high yields. The overall transformation consists of an initial C−N coupling, demonstrated using traditional Ullmann or Buchwald−Hartwig conditions, followed by an in situ oxetane ring opening. A range of functionality is tolerated on the aryl ring, and the cyclization exposes a pendant hydroxymethyl substituent, providing opportunities for further functionalization.

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A mild and metal-free synthesis of chiral 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazines

Cited by 3 publications

References 18 publications

Construction of Benzo‐Fused Heterocycles by Epoxide–Heteronucleophile Cyclization: Applications in the Synthesis of Natural Products and Designed Molecules

Construction of Benzo‐Fused Heterocycles by Epoxide–Heteronucleophile Cyclization: Applications in the Synthesis of Natural Products and Designed Molecules

Three-membered ring systems

Tandem Amination/Oxetane Ring Opening toward Benzomorpholines

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