Indolinol-catalyzed asymmetric Michael reaction of aldehydes to nitroalkenes in brine. Issue 9 (1st June 2016)

• Record Type: Journal Article
• Authors: Hu, Xin; Wei, Yi-Fei; Wu, Nan; Jiang, Zhiguo; Liu, Can; Luo, Ren-Shi
• Is Part Of: Tetrahedron, asymmetry. Volume 27:Issue 9/10(2016)
• Page Start: 420
• Page End: 427
• Publication Date: 2016-06-01
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2016.03.006
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: (2 S, 3 aS, 7 aS )-PerhydroindolinolA facilitated the reaction of a wide range of aldehyde and nitroalkene substrates to provide Michael adducts with excellent enantioselectivities (up to 98% ee ), excellent yields and high diastereoselectivities ( syn / anti up to 99:1). Our results indicated that perhydroindolinols were also highly efficient organocatalysts for asymmetric Michael reactions in brine, while also being environmentally friendly. Abstract : CatalystB : C15 H31 NOSi [ α ]D 20 = −9.5 ( c 0.10, CHCl3 ) Abstract : CatalystC : C25 H35 NOSi [ α ]D 20 = −8.7 ( c 0.25, CHCl3 )