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Enantioselective Organocatalytic Michael Addition of Aldehydes to Nitroethylene: Efficient Access to γ2-Amino Acids
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Abstract
Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene catalyzed by (S)-diphenylprolinol silyl ether provides β-substituted-δ-nitroalcohols in nearly optically pure form (96−99% ee). The Michael adducts bear a single substituent adjacent to the carbonyl and can be efficiently converted to protected γ2-amino acids, which are essential for the systematic conformational studies of γ-peptide foldamers.
Citing Articles
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This article has been cited by 16 ACS Journal articles (5 most recent appear below).
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Competition between Amide Stacking and Intramolecular H Bonds in γ-Peptide Derivatives: Controlling Nearest-Neighbor Preferences
William H. James, III, Evan G. Buchanan, Li Guo, Samuel H. Gellman, and Timothy S. ZwierThe Journal of Physical Chemistry A2011 115 (43), 11960-11970Competition between Amide Stacking and Intramolecular H Bonds in γ-Peptide Derivatives: Controlling Nearest-Neighbor Preferences
William H. James, III, Evan G. Buchanan, Li Guo, Samuel H. Gellman, and Timothy S. ZwierThe Journal of Physical Chemistry A2011 115 (43), 11960-11970Resonant two-photon ionization (R2PI), IR-UV holeburning (IR-UV), and resonant ion-dip infrared spectroscopy (RIDIRS) have been used to record mass-selected, single-conformation ultraviolet and infrared spectra of three simple diamide derivatives of γ-...
Highly Enantioselective γ-Amination of α,β-Unsaturated Acyl Chlorides with Azodicarboxylates: Efficient Synthesis of Chiral γ-Amino Acid Derivatives
Li-Tao Shen, Li-Hui Sun, and Song YeJournal of the American Chemical Society2011 133 (40), 15894-15897Highly Enantioselective γ-Amination of α,β-Unsaturated Acyl Chlorides with Azodicarboxylates: Efficient Synthesis of Chiral γ-Amino Acid Derivatives
Li-Tao Shen, Li-Hui Sun, and Song YeJournal of the American Chemical Society2011 133 (40), 15894-15897The cinchona alkaloid-catalyzed γ-amination of α,β-unsaturated acyl chlorides with azodicarboxylates to give the corresponding dihydropyridazinones in good yields with high enantioselectivities has been developed. Reductive ring opening of the ...
Organocatalytic Asymmetric Michael Addition of 1-Acetylindolin-3-ones to α,β-Unsaturated Aldehydes: Synthesis of 2-Substituted Indolin-3-ones
Yao-Zong Liu, Jie Zhang, Peng-Fei Xu, and Yong-Chun LuoThe Journal of Organic Chemistry2011 76 (18), 7551-7555Organocatalytic Asymmetric Michael Addition of 1-Acetylindolin-3-ones to α,β-Unsaturated Aldehydes: Synthesis of 2-Substituted Indolin-3-ones
Yao-Zong Liu, Jie Zhang, Peng-Fei Xu, and Yong-Chun LuoThe Journal of Organic Chemistry2011 76 (18), 7551-7555A highly efficient asymmetric Michael addition of 1-acetylindolin-3-ones to α,β-unsaturated aldehydes is developed to afford 2-substituted indolin-3-one derivatives in high yields (up to 94%) with good stereoselectivities (up to 11:1 dr and 96% ee). The ...
One-Pot Asymmetric Synthesis of γ-Nitroaldehydes from Aldehydes and Nitroalkanes through a Catalytic Tandem Reaction Using an Amino Acid Lithium Salt
Masanori Yoshida, Naoki Kitamikado, Hiroto Ikehara, and Shoji HaraThe Journal of Organic Chemistry2011 76 (7), 2305-2309One-Pot Asymmetric Synthesis of γ-Nitroaldehydes from Aldehydes and Nitroalkanes through a Catalytic Tandem Reaction Using an Amino Acid Lithium Salt
Masanori Yoshida, Naoki Kitamikado, Hiroto Ikehara, and Shoji HaraThe Journal of Organic Chemistry2011 76 (7), 2305-2309One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes was achieved by a catalytic tandem reaction using a primary amino acid lithium salt, O-tert-butyldiphenylsilyl l-tyrosine lithium salt, as a catalyst. Various aryl, alkenyl, ...
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History
- Published In Issue April 30, 2008
- Article ASAPApril 04, 2008
- Received: January 15, 2008
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