Biocatalytic synthesis of allylic and allenyl sulfides via a myoglobin-catalyzed Doyle-Kirmse reaction

• Published in: Angewandte Chemie International Edition
• Main Authors: Tyagi, Vikas, Sreenilayam, Gopeekrishnan, Bajaj, Priyanka, Tinoco, Antonio, Fasan, Rudi
• Format: Text
• Language: English
• Published: 2016
• Subjects: Article; Doyle; Sperm whale
• Online Access: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5189672/; http://www.ncbi.nlm.nih.gov/pubmed/27647732; https://doi.org/10.1002/anie.201607278

The first example of a biocatalytic [2,3]-sigmatropic rearrangement reaction involving allylic sulfides and diazo reagents (Doyle-Kirmse reaction) is reported. Engineered variants of sperm whale myoglobin catalyze this synthetically valuable C–C bond forming transformation with high efficiency and p...