Enantiodivergent Rh‐Catalyzed Reductive Hydroformylation of Alkenyl Boronic Esters
Abstract
Abstract We herein report the first enantioselective Rh‐catalyzed reductive hydroformylation of alkenyl boronic esters. By employing either “camouflage” or “direct” reductive AHF strategy, enantiodivergent synthesis of chiral γ ‐boryl alcohols has been developed for the first time in high yields and excellent enantioselectivities with alkene 1,2‐diboronic esters or alkenyl boronic esters as the starting materials using rhodium/Ph‐BPE as the catalyst. The method has enjoyed high chemo‐selectivity, good functional group compatibility, and broad substrate scope. The chiral γ ‐boryl alcohol or diol products are versatile building blocks applicable to the synthesis of a series of APIs including (S)‐tolterodine, (S)‐dapoxetine, and (R)‐atomaxetine. DFT calculation has revealed the origin of enantiodivergence of Rh‐catalyzed reductive AHF of alkenyl boronic esters with Ph‐BPE as the chiral ligand. The transformation is promised to provide great synthetic potential in both academia and industry.
Read the paper
Related studies
- Improving the translation of search strategies using the Polyglot Search Translator: a randomized controlled trial
- Nutritional, Physical, Cognitive, and Combination Interventions and Frailty Reversal Among Older Adults: A Randomized Controlled Trial
- Clinical characteristics and risk factors associated with COVID-19 severity in patients with haematological malignancies in Italy: a retrospective, multicentre, cohort study
- A randomized, controlled trial of oral propranolol in infantile hemangioma
- Clinical phenotypes of delirium during critical illness and severity of subsequent long-term cognitive impairment: a prospective cohort study
- Increased physical activity improves sleep and mood outcomes in inactive people with insomnia: a randomized controlled trial
Go deeper in Evidence Hub
Evidence Hub adds a study data sheet (design, sample size, evidence level, key numbers), an AI summary and a chat grounded in the paper's text.