Unknown

Dataset Information

0

Biocatalytic Conversion of Cyclic Ketones Bearing ?-Quaternary Stereocenters into Lactones in an Enantioselective Radical Approach to Medium-Sized Carbocycles.


ABSTRACT: Cyclic ketones bearing ?-quaternary stereocenters underwent efficient kinetic resolution using cyclohexanone monooxygenase (CHMO) from Acinetobacter calcoaceticus. Lactones possessing tetrasubstituted stereocenters were obtained with high enantioselectivity (up to >99?%?ee) and complete chemoselectivity. Preparative-scale biotransformations were exploited in conjunction with a SmI2 -mediated cyclization process to access complex, enantiomerically enriched cycloheptan- and cycloctan-1,4-diols. In a parallel approach to structurally distinct products, enantiomerically enriched ketones from the resolution with an ?-quaternary stereocenter were used in a SmI2 -mediated cyclization process to give cyclobutanol products (up to >99?%?ee).

SUBMITTER: Morrill C 

PROVIDER: S-EPMC6055628 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

Similar Datasets

| S-EPMC8602376 | biostudies-literature
| S-EPMC6555830 | biostudies-other
| S-EPMC8456945 | biostudies-literature
| S-EPMC5391976 | biostudies-literature
| S-EPMC9629005 | biostudies-literature
| S-EPMC5651675 | biostudies-literature
| S-EPMC5634709 | biostudies-literature
| S-EPMC9158264 | biostudies-literature
| S-EPMC5390761 | biostudies-literature
| S-EPMC2747361 | biostudies-literature