Lipase‐Catalyzed tert‐ Butoxycarbonylation of Alcohols Using Boc 2 O

• Published in: ChemistrySelect
• Main Authors: Kishi, Naoki, Kojima, Hideo
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2019
• Subjects: Rugosa; Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/slct.201902423; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fslct.201902423; https://onlinelibrary.wiley.com/doi/pdf/10.1002/slct.201902423; https://onlinelibrary.wiley.com/doi/full-xml/10.1002/slct.201902423

Abstract Lipase‐catalyzed tert‐ butoxycarbonylation of alcohols using di ‐tert‐ butyl dicarbonate (Boc 2 O) was developed. Aspergillus niger lipase, Burkholderia cepacia lipase, Pseudomonas fluorescens lipase, Candida rugosa lipase, and Candida antarctica lipase B were examined. The reaction of benzyl alcohol with Boc 2 O proceeded smoothly in the presence of Candida rugosa lipase in hexane to produce benzyl tert ‐butyl carbonate in a good yield. Similarly, the tert‐ butoxycarbonylation reactions of 4‐methylbenzyl alcohol, 4‐methoxybenzyl alcohol, 4‐chlorobenzyl alcohol, 4‐bromobenzyl alcohol, 4‐nitrobenzyl alcohol, 2‐phenylethanol, 3‐phenyl‐1‐propanol, cinnamyl alcohol, and 2‐naphthalene methanol using Boc 2 O in the presence of Candida rugosa lipase in hexane resulted in very good to‐excellent yields of the corresponding tert‐ butoxycarbonylated alcohols.