| Institution: | 1. PSL University, Chimie ParisTech, CNRS UMR 8060, Institute of Chemistry for Life and Health Sciences, CSB2D Team, 75005 Paris, France
SEQENS, 2-8 rue de Rouen ZI de Limay-Porcheville, 78440 Porcheville, France;2. PSL University, Chimie ParisTech, CNRS UMR 8060, Institute of Chemistry for Life and Health Sciences, CSB2D Team, 75005 Paris, France;3. SEQENS, 2-8 rue de Rouen ZI de Limay-Porcheville, 78440 Porcheville, France |
| Abstract: | A straightforward method to access novel families of enantioenriched cis-monofluorinated carbocyclic alcohols has been developed through ATH/DKR in up to 97 % yield, up to 99 : 1 dr and enantioinductions up to 97 % ee. Trans-difluorinated indans, tetrahydronaphthalenes, tetrahydroquinolines and chromans have been synthesized as well by deoxofluorination of the corresponding cis-fluoro alcohols. The reaction was performed on a series of variously substituted 3-fluorochromanols, 3-fluorotetrahydroquinolinols, 2-fluoro inden-1-ols and 2-fluoro 1,2,3,4-tetrahydronaphthalen-1-ols in up to 86 % yields, with diastereoselectivities up to 97 : 3 and enantioselectivities up to >99 % ee. |
