Journal ArticleDOI
Enantiospecific Photochemical Norrish/Yang Type II Reaction of Nonbiaryl Atropchiral α-Oxoamides in Solution—Axial to Point Chirality Transfer
Anoklase Jean-Luc Ayitou,Josepha L. Jesuraj,Nilotpal Barooah,Angel Ugrinov,Jayaraman Sivaguru +4 more
TLDR
Alpha-oxoamides 1 with o-tert-butyl substitution on the N-phenyl moiety were found to be stable axially chiral atropisomers and undergo enantiospecific photochemical gamma-Hydrogen abstraction in CHCl(3) to yield beta-lactams with high enantioselectivity.Abstract:
Alpha-oxoamides 1 with o-tert-butyl substitution on the N-phenyl moiety were found to be stable axially chiral atropisomers. These axially chiral alpha-oxoamides undergo enantiospecific photochemical gamma-Hydrogen abstraction in CHCl(3) to yield beta-lactams with high enantioselectivity (e.r. approximately 90:10) in solution. The extent of enantioselectivity was found to be dependent on the reaction temperature.read more
Citations
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Journal ArticleDOI
Nonbiaryl and Heterobiaryl Atropisomers: Molecular Templates with Promise for Atropselective Chemical Transformations
Journal ArticleDOI
Supramolecular Photochemistry as a Potential Synthetic Tool: Photocycloaddition.
TL;DR: It is believed that the supramolecular photochemistry expounded here has a momentous role as a synthetic tool in the future, since no other reagent would be more sustainable than light and no other medium greener than water.
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Catalytic Asymmetric Synthesis of Axially Chiral o-Iodoanilides by Phase-Transfer Catalyzed Alkylations
TL;DR: Catalytic asymmetric synthesis of axially chiral o-iodoacrylanilides and N-allyl-o-iodoanilides as useful chiral building blocks was achieved via chiral quaternary ammonium salt-catalyzed N-alkylations under phase-transfer conditions.
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Axial-to-central chirality transfer in cyclization processes
TL;DR: Highly functionalized enantiopure carbocycles and heterocycles were prepared using the chirality transfer strategy and the transformations of configurationally stable substrates take place with high regio- and stereo-selectivity.
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Atroposelective Catalytic Asymmetric Allylic Alkylation Reaction for Axially Chiral Anilides with Achiral Morita–Baylis–Hillman Carbonates
TL;DR: A broad range of axially chiral anilide products with different acyl groups, such as substituted phenyl, naphthyl, alkyl, enyl, styryl, and benzyl, were generated with very good yields, moderate to excellent cis: trans ratios, and good to excellent enantioselectivities.
References
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Synthesis of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP), an atropisomeric chiral bis(triaryl)phosphine, and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of .alpha.-(acylamino)acrylic acids
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Modified BINOL ligands in asymmetric catalysis.
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Asymmetric photoreactions within zeolites: role of confinement and alkali metal ions.
Jayaraman Sivaguru,Arunkumar Natarajan,Lakshmi S. Kaanumalle,J. Shailaja,Sundararajan Uppili,Abraham Joy,Vaidhyanathan Ramamurthy +6 more
TL;DR: Results of ab initio computations have allowed us to gain an insight into the observed selectivity within zeolites, which shows no asymmetric induction in solution.
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Asymmetric Induction during Energy Transfer1
George S. Hammond,Ronald S. Cole +1 more
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Chirality Control in Photochemical Reactions: Enantioselective Formation of Complex Photoproducts in Solution
Christiane Müller,Thorsten Bach +1 more
TL;DR: Synthetic applications show that the area of enantioselective photochemistry has left the state of infancy and is about to become a mature but continuously challenging area of modern chemistry.