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Chiral N-Heterocyclic Carbene Catalyzed Staudinger Reaction of Ketenes with Imines: Highly Enantioselective Synthesis of N-Boc β-Lactams
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Abstract
N-Heterocyclic carbenes (NHCs) were demonstrated to be efficient catalysts for the Staudinger reaction of ketenes with N-tosyl, N-benzyloxycarbonyl, or N-tert-butoxycarbonyl imines. Chiral NHC 8b, conveniently prepared from l-pyroglutamic acid, catalyzed the reactions of arylalkylketenes with a variety of N-tert-butoxycarbonyl arylimines to give the corresponding cis-β-lactams in good yields with good diastereoselectivities and excellent enantioselectivities (up to 99% ee). Two possible catalytic pathways, initiated by the addition of NHC to ketenes or imines, were discussed.
Citing Articles
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This article has been cited by 23 ACS Journal articles (5 most recent appear below).
NHC-Catalyzed Enantioselective [2 + 2] and [2 + 2 + 2] Cycloadditions of Ketenes with Isothiocyanates
Xiao-Na Wang, Li-Tao Shen, and Song YeOrganic Letters2011 13 (24), 6382-6385NHC-Catalyzed Enantioselective [2 + 2] and [2 + 2 + 2] Cycloadditions of Ketenes with Isothiocyanates
Xiao-Na Wang, Li-Tao Shen, and Song YeOrganic Letters2011 13 (24), 6382-6385The enantioselective N-heterocyclic carbene-catalyzed formal [2 + 2] and [2 + 2 + 2] cycloaddition of ketenes and isothiocyanates were developed. Reaction with N-aryl isothiocyanates at room temperature favors the [2 + 2] cycloaddition, while reaction ...
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 ...
Formal Diels–Alder Reactions of Chalcones and Formylcyclopropanes Catalyzed by Chiral N-Heterocyclic Carbenes
Hui Lv, Junming Mo, Xinqiang Fang, and Yonggui Robin ChiOrganic Letters2011 13 (19), 5366-5369Formal Diels–Alder Reactions of Chalcones and Formylcyclopropanes Catalyzed by Chiral N-Heterocyclic Carbenes
Hui Lv, Junming Mo, Xinqiang Fang, and Yonggui Robin ChiOrganic Letters2011 13 (19), 5366-5369Highly enantioselective (formal) hetero-Diels–Alder reactions between chalcones and formylcyclopropanes are disclosed. The challenging N-heterocyclic carbene (NHC)-bounded enolate intermediates from formylcyclopropanes were captured for new C–C bond ...
Enantioselective Synthesis of Dihydropyridinones via NHC-Catalyzed Aza-Claisen Reaction
Benedikt Wanner, Jessada Mahatthananchai, and Jeffrey W. BodeOrganic Letters2011 13 (19), 5378-5381Enantioselective Synthesis of Dihydropyridinones via NHC-Catalyzed Aza-Claisen Reaction
Benedikt Wanner, Jessada Mahatthananchai, and Jeffrey W. BodeOrganic Letters2011 13 (19), 5378-5381N-Heterocyclic carbene catalyzed aza-Claisen annulations of enals or their α′-hydroxyenone surrogates with vinylogous amides afford dihydropyridinones. The reaction proceeds with a broad range of substrates, and no nitrogen protecting group is required.
Entrapment and Kinetic Resolution of Stabilized Axial and Equatorial Conformers of Spiro-β-lactams
Naveen Anand, Bhahwal A. Shah, Munish Kapoor, Rajinder Parshad, Rattan L. Sharma, Maninder S. Hundal, Ajay P. S. Pannu, Prasad V. Bharatam, and Subhash C. TanejaThe Journal of Organic Chemistry2011 76 (15), 5999-6006Entrapment and Kinetic Resolution of Stabilized Axial and Equatorial Conformers of Spiro-β-lactams
Naveen Anand, Bhahwal A. Shah, Munish Kapoor, Rajinder Parshad, Rattan L. Sharma, Maninder S. Hundal, Ajay P. S. Pannu, Prasad V. Bharatam, and Subhash C. TanejaThe Journal of Organic Chemistry2011 76 (15), 5999-6006The facile synthesis of the stabilized axial and equatorial conformers of spiro-β-lactams was achieved via entrapment of cyclohexanone imines (Schiff bases) with acetoxyacetyl chloride in a [2 + 2]-cycloaddition reaction followed by their kinetic ...
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History
- Published In Issue January 17, 2008
- Received November 15, 2007
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