Efficient Access to Chiral β‐Borylated Carboxylic Esters via Rh‐Catalyzed Hydrogenation. Issue 12 (11th April 2019)

• Record Type: Journal Article
• Authors: Liu, Gang; Li, Anqi; Qin, Xueyuan; Han, Zhengyu; Dong, Xiu‐Qin; Zhang, Xumu
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 12(2019)
• Page Start: 2844
• Page End: 2848
• Publication Date: 2019-04-11
• Subjects: Asymmetric hydrogenation -- β-boryl-α, β-unsaturated esters -- chiral β-borylated carboxylic esters -- enantioselectivity -- bisphosphine ligand; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900161
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Rh/bisphosphine−thiourea ligand (ZhaoPhos)‐catalyzed asymmetric hydrogenation of ( Z )‐β‐substituted‐β‐boryl‐α, β‐unsaturated esters was successfully developed, furnishing a variety of chiral β‐borylated carboxylic esters with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). The gram‐scale asymmetric hydrogenation was performed efficiently in the presence of only 0.05 mol% (S/C=2 000) catalyst loading with full conversion, 99% yield and 99% ee. Moreover, the hydrogenation product was easily converted to other versatile synthetic intermediates, such as methyl ( S )‐3‐hydroxy‐3‐phenylpropanoate and methyl ( S )‐3‐(furan‐2‐yl)‐3‐phenylpropanoate. Abstract :