Details

Autor(en) / Beteiligte

• Huang, Xin
• Liu, Miao
• Jasinski, Jerry P.
• Peng, Bo
• Zhang, Wei

Titel

Recyclable Organocatalysts for a One‐Pot Asymmetric Synthesis of 2‐Fluorocyclohexanols Bearing Six Contiguous Stereocenters

Ist Teil von

• Advanced synthesis & catalysis, 2017-06, Vol.359 (11), p.1919-1926

Ort / Verlag

Heidelberg: Wiley Subscription Services, Inc

Erscheinungsjahr

2017

Quelle

Wiley Blackwell Single Titles

Beschreibungen/Notizen

• A recyclable fluorous bifunctional Cinchona alkaloid/thiourea‐catalyzed quadruple fluorination/Michael/Michael/aldol sequence has been developed for the one‐pot synthesis of cyclohexanols bearing six contiguous stereocenters including a fluorinated tertiary carbon. By using readily available starting materials including β‐keto esters, β‐nitrostyrenes, and α,β‐unsaturated aldehydes, fully functionalized cyclohexanols were synthesized in 52–80% yields with up to 99% ee and >20:1 dr. The fluorous catalyst could be easily recovered by fluorous solid‐phase extraction in 94–97% yield and >98% purity. In addition to the high synthetic efficiency achieved through the pot economic reactions, other green techniques such as transition metal‐free catalysis and catalyst recovery are also employed.