Asymmetric Organocatalytic Synthesis of Highly Substituted Cyclohexenols by Domino Double-Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles

作者：Jang Yeong Jiunn; Chen Yu Shan; Lee Chia Jui; Chen Chi Han; Reddy Ganapuram Madhusudhan; Ko Chi Ting; Lin Wenwei^*

来源：European Journal of Organic Chemistry, 2015, 2015(9): 2066-2074.

DOI：10.1002/ejoc.201403677

• Organocatalysis
• Domino reactions
• Michael addition
• Enones
• Carbocycles
• Alkaloids

A facile asymmetric synthetic protocol to afford 2,6-disubstituted 4-hydroxy-3-oxocyclohex-3-ene-1,1-dicarbonitriles has been developed through the domino double-Michael addition of 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles using quinine as the catalyst. This simple organocatalytic domino process provides access to various highly functionalized chiral 4-hydroxy-3-oxocyclohex-3-enes, which are the rarely reported chiral diketo cyclohexane analogues, in moderate-to-good yields and enantioselectivities and with excellent diastereoselectivities (>25:1 dr).

• 出版日期2015-3
• 单位中国医科大学