Domino Michael/Michael Reaction for the Formation of Chiral Spirocycles Using a Diphenylprolinol Silyl Ether

Abstract

A domino Michael/Michael reaction of 2‐(2‐formylethyl)naphthalene‐1,4‐dione and nitroalkene was catalyzed by diphenylprolinol silyl ether to afford functionalized spiro[cyclopentane‐1,2′(1′H)‐naphthalene] derivatives with four continuous stereocenters in good yields with excellent diastereo‐ and enantioselectivities.

Stereoselective Domino Reactions in the Synthesis of Spiro Compounds

“…A remarkably example of a Michael/Michael reaction between a naphthoquinone and nitroalkenes was recently presented by Hayashi and co-workers. 20 In this work functionalized spirocyclopentane-1,2′(1′ H )-naphthalene derivatives with four continuous stereocenters were synthesized with excellent diastereo- and enantioselectivities (Scheme 8 ). The reaction consists of the domino Michael/ exo -Michael reaction of 2-(2-formylethyl)naphthalene-1,4-dione ( 89 ) and nitroalkenes 90 catalyzed by diphenylprolinol silyl ether 61a .…”

Cobalt Coordination Polymers Offering Hydrogen Bonding Cavities as Efficient Catalysts for Coupling Reactions

“…[42][43][44][45] A large number of catalytic protocols have been developed for such reactions, either by utilizing direct approaches or through domino reactions for the synthesis of desirable molecules. [46,47] In particular, Friedel Crafts reactions (FCRs) involving poorly nucleophilic indoles with nitro-olefins as the Michael acceptor have emerged as the pertinent class of MARs resulting in the synthesis of versatile CÀ C coupled compounds. [48][49][50][51][52][53][54][55] Such coupling reactions generate alkylated indoles that are notable precursors for the synthesis of biologically active alkaloids and tryptamine derivatives.…”

“…From a pool of C−C bond forming reactions, Michael addition reactions (MARs) have gained widespread attention [42–45] . A large number of catalytic protocols have been developed for such reactions, either by utilizing direct approaches or through domino reactions for the synthesis of desirable molecules [46,47] . In particular, Friedel Crafts reactions (FCRs) involving poorly nucleophilic indoles with nitro‐olefins as the Michael acceptor have emerged as the pertinent class of MARs resulting in the synthesis of versatile C−C coupled compounds [48–55] .…”

Exploration of chromophores for a VCD couplet in a spectrally transparent infrared region for biomolecules

“…17,18 On the basis of this correlation, structures of various molecules have been analysed with or without introduction of extra carbonyl chromophores, in a similar manner to the applications of the ECD exciton chirality method. [19][20][21][22][23][24][25][26][27][28][29][30] VCD couplet is also used for signal augmentation that leads to VCD measurements with reduced sample amount and with a short acquisition time. For example, VCD couplet of 1 was observed even at a concentration of 2.5 mM.…”