A practical and highly enantioselective catalytic Reformatsky reaction with aldehydes using a cheap, commercially available aminoalcohol as ligand is described.
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Synthetic studies towards naturally occurring sesquiterpene capillosanane V: construction of a fully functionalized cycloheptane core through an intramolecular Reformatsky reaction.
Org Biomol Chem
January 2025
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, 721302, India.
We herein disclose the synthesis of a bicyclo [5,1,0]-octane ring system consisting of a cycloheptane core fused with a cyclopropane unit of naturally occurring sesquiterpene capillosanane V. Initially, an unsuccessful RCM reaction of a properly functionalized bis-olefinic precursor was attempted. Finally, an intramolecular Reformatsky reaction was employed to construct the cycloheptane core present in the target structure.
View Article and Find Full Text PDFChromium Catalyzed Asymmetric Reformatsky Reaction.
Angew Chem Int Ed Engl
August 2024
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, Hangzhou, 310030, Zhejiang Province, China.
This study describes an unprecedented chromium-catalyzed asymmetric Reformatsky reaction, enabling the synthesis of chiral β-hydroxy carbonyl compounds from α-chlorinated or α-brominated esters and amides. By employing a chiral chromium/diarylamine bis(oxazoline) catalyst, we achieved relatively broad functional group tolerance. Distinct from known reports, the protocol operates under both classical and photoredox conditions, facilitated by the in situ formation of a nucleophilic chiral chromium intermediate through a radical-polar crossover mechanism.
View Article and Find Full Text PDFCobalt-Catalyzed Enantioselective Reductive α-Chloro-Carbonyl Addition of Ketimine to Construct the β-Tertiary Amino Acid Analogues.
Angew Chem Int Ed Engl
June 2024
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China.
β-Tertiary amino acid derivatives constitute one of the most frequently occurring units in natural products and bioactive molecules. However, the efficient asymmetric synthesis of this motif still remains a significant challenge. Herein, we disclose a cobalt-catalyzed enantioselective reductive addition reaction of ketimine using α-chloro carbonyl compound as a radical precursor, providing expedient access to a diverse array of enantioenriched β-quaternary amino acid analogues.
View Article and Find Full Text PDFPhotoredox-Catalyzed Generation of Tertiary Anions from Primary Amines via a Radical Polar Crossover.
Angew Chem Int Ed Engl
February 2024
Department of Chemistry, Columbia University, New York, NY 10027, USA.
A method for the generation of tertiary carbanions via a deaminative radical-polar crossover is reported using redox active imines from α-tertiary primary amines. A variety of benzylic amines and amino esters can be used in this approach, with the latter engaging in a novel "aza-Reformatsky" reaction. Electronic trends correlate the stability of the resulting carbanion with reaction efficiency.
View Article and Find Full Text PDFPhotoinduced reductive Reformatsky reaction of α-haloesters and aldehydes or ketones by cooperative dual-metal catalysis.
Chem Commun (Camb)
December 2023
State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
A photoinduced reductive Reformatsky reaction by cooperative dual-metal catalysis is described. This methodology enables the implementation of this venerable reaction in environmentally friendly conditions, obviating the need for a stoichiometric amount of metals. A broad range of synthetically useful β-hydroxy esters can be efficiently prepared in moderate to high yields using this protocol.
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