Indolinol-catalyzed asymmetric Michael reaction of aldehydes to nitroalkenes in brine

(2S,3aS,7aS)-Perhydroindolinol A 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.

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Catalyst BC15H31NOSi[α]D20 = −9.5 (c 0.10, CHCl3)

Catalyst CC25H35NOSi[α]D20 = −8.7 (c 0.25, CHCl3)