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Dr. Qipu Dai, Dr. Hadi Arman and Prof. Dr. John Cong-Gui Zhao One-Pot Sequential Organocatalysis: Highly Stereoselective Synthesis of Trisubstituted Cyclohexanols Chemistry - A European Journal 19

Article first published online: 13 DEC 2012 | DOI: 10.1002/chem.201203104

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A poor reaction saved! The tandem Henry–Michael reaction of nitromethane and 7-oxo-hept-5-en-1-als catalyzed by quinidine thiourea 1 generates a mixture of diastereomers. A subsequent one-pot tetramethyl guanidine (TMG)-catalyzed tandem retro-Henry–Henry reaction on this diastereomeric mixture provided the corresponding trisubstituted cyclohexanols in high enantioselectivities (up to 96 % ee) and excellent diastereoselectivities (>99:1 d.r.; see scheme).

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