A chemoenzymatic route to chiral siloxanes

作者：Naoum Ravi; Seguin Jacqueline P; Trant John F; Frampton Mark B; Hudlicky Tomas; Zelisko Paul M^*

来源：Tetrahedron, 2016, 72(27-28): 4027-4031.

DOI：10.1016/j.tet.2016.05.032

• Biotransformations
• Chemoenzymatic
• Chirality
• Transesterification
• Siloxane

An approach employing two enzymes-toluene dioxygenase and immobilized lipase B from Candida antarctica (N435)-was explored as a potential biocatalytic method for the coupling of chiral diols with siloxane species. Analysis of reaction mixtures using H-1 NMR spectroscopy suggested that up to 66% consumption of the siloxane starting materials had occurred. Oligomeric species were observed and chiral products from the coupling of a cyclic diol with a siloxane molecule were isolated and characterized by IVIALDI-ToF MS and GPC.
Immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus were also explored as potential catalysts for the coupling reactions, however, their use only returned starting material.

• 出版日期2016-7-7