The Role of Protective Groups in Organic Synthesis

doi:10.1002/9781118905074.ch01

Greene's Protective Groups in Organic Synthesis 2014

DOI: 10.1002/9781118905074.ch01

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The Role of Protective Groups in Organic Synthesis

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Cited by 4 publications

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Phenacyl Xanthates: A Photoremovable Protecting Group for Alcohols under Visible Light

Yang

2019

Asian J Org Chem

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The utility of phenacyl xanthates for the protection of hydroxyl groups is reported herein. Phenacyl xanthates are readily prepared via a one‐pot procedure, which employs the commercially available, inexpensive 2‐bromoacetophenone and carbon disulphide. The introduction of phenylcarboxymethyl dithiocarbonates could be achieved in good to excellent yield in the presence of ester group or ketal group. The hydroxyl group can be released in the presence of ethidine under irradiation of visible light without photocatalyst. The phenacyl xanthates could be selectively removed without affecting a series of common protecting groups, such as benzoate, tetrahydropyran and ketal groups. Finally, a plausible mechanism of photocleavage of phenacyl xanthates has been discussed.

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Phenacyl Xanthates: A Photoremovable Protecting Group for Alcohols under Visible Light

Yang

2019

Asian J Org Chem

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Regioselective Anomeric O‐Benzyl Deprotection in Carbohydrates

2021

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Chemoselective N-acetylation of primary aliphatic amines promoted by pivalic or acetic acid using ethyl acetate as an acetyl donor

Yoshida

Kawamura

Nakata

2017

Tetrahedron Letters

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The Role of Protective Groups in Organic Synthesis

Cited by 4 publications

References 43 publications

Phenacyl Xanthates: A Photoremovable Protecting Group for Alcohols under Visible Light

Phenacyl Xanthates: A Photoremovable Protecting Group for Alcohols under Visible Light

Regioselective Anomeric O‐Benzyl Deprotection in Carbohydrates

Chemoselective N-acetylation of primary aliphatic amines promoted by pivalic or acetic acid using ethyl acetate as an acetyl donor

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