Cyclohexylcarbonitriles: Diastereoselective Arylations with TMPZnCl· LiCl

…, S Bernhardt, J Heppekausen, P Knochel…

文献索引：Duez, Stephanie; Bernhardt, Sebastian; Heppekausen, Johannes; Fleming, Fraser F.; Knochel, Paul Organic Letters, 2011 , vol. 13, # 7 p. 1690 - 1693

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被引用次数: 4

摘要

Deprotonating substituted cyclohexanecarbonitriles with TMPZnCl· LiCl affords zincated nitriles that diastereoselectively couple with aryl bromides in the presence of catalytic Pd (OAc) 2 and S-Phos. Steric and electronic effects influence the diastereoselectivity; 4-t-butyl-, 4-TBSO-, and 2-Me-cyclohexanecarbonitriles exert virtually complete diastereocontrol whereas modest diastereoselectivity is observed with 4-i-Pr-, 4-Me-, and 3-Me- ...