Enantioselective Synthesis of Allylboronates and Allylic Alcohols by Copper‐Catalyzed 1,6‐Boration |
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| Authors: | Dr Yunfei Luo Iain D Roy Amaël G E Madec Prof Hon Wai Lam |
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| Institution: | 1. EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ (UK);2. School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD (UK) http://www.nottingham.ac.uk/～pczhl |
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| Abstract: | Chiral secondary allylboronates are obtained in high enantioselectivities and 1,6:1,4 ratios by the copper‐catalyzed 1,6‐boration of electron‐deficient dienes with bis(pinacolato)diboron (B2(pin)2). The reactions proceed efficiently using catalyst loadings as low as 0.0049 mol %. The allylboronates may be oxidized to the allylic alcohols, and can be used in stereoselective aldehyde allylborations. This process was applied to a concise synthesis of atorvastatin, in which the key 1,6‐boration was performed using only a 0.02 mol % catalyst loading. |
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| Keywords: | 1 6‐addition asymmetric catalysis boron copper enantioselectivity |
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