Journal ArticleDOI
N-tert-butanesulfinyl imines: versatile intermediates for the asymmetric synthesis of amines.
TLDR
N-tert-Butanesulfinyl aldimines 3 and ketimines 4 are exceedingly versatile intermediates for the asymmetric synthesis of amines and provide a new family of ligands for asymmetric catalysis.Abstract:
N-tert-Butanesulfinyl aldimines 3 and ketimines 4 are exceedingly versatile intermediates for the asymmetric synthesis of amines. The N-tert-butanesulfinyl imines are prepared in high yields by condensing enantiomerically pure tert-butanesulfinamide 1, which is readily available in either configuration, with a wide range of aldehydes and ketones. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment of the product with acid. A wide range of highly enantioenriched amines, including α-branched and α,α-dibranched amines, α- and β-amino acids, 1,2- and 1,3-amino alcohols, and α-trifluoromethyl amines, are efficiently synthesized using this methodology. In addition, N-tert-butanesulfinyl imine derivatives provide a new family of ligands for asymmetric catalysis.read more
Citations
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Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions.
TL;DR: The motivation for studying Pd-catalyzed C-H functionalization assisted by weakly coordinating functional groups is discussed, and efforts to bring reactions of this type to fruition are chronicle.
Journal ArticleDOI
Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas
Yu Zhou,Jiang Wang,Zhanni Gu,Shuni Wang,Wei Zhu,José Luis Aceña,Vadim A. Soloshonok,Kunisuke Izawa,Hong Liu +8 more
TL;DR: Compounds Currently in Phase II−III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas is presented.
Journal ArticleDOI
Transition metal-catalyzed C–H activation reactions: diastereoselectivity and enantioselectivity
TL;DR: This critical review discusses historical and contemporary research in the field of transition metal-catalyzed carbon-hydrogen (C-H) bond activation through the lens of stereoselectivity, placing an emphasis on reactions that are (or may soon become) relevant in the realm of organic synthesis.
Journal ArticleDOI
Lewis Base Catalysis in Organic Synthesis
TL;DR: It has become increasingly apparent that the behavior of Lewis bases as agents for promoting chemical reactions is not merely as an electronic complement of the cognate Lewis acids: in fact Lewis bases are capable of enhancing both the electrophilic and nucleophilic character of molecules to which they are bound.
Journal ArticleDOI
Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?
Dean G. Brown,Jonas Boström +1 more
TL;DR: It is shown that current practices result in overpopulation of certain types of molecular shapes to the exclusion of others using simple PMI plots, which could help catalyze improvements in integration of new synthetic methodologies as well as new library design.
References
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Journal ArticleDOI
Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines
TL;DR: In this article, high yielding and highly diastereoselective methods for 1,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) and Ntertbutane sulfinamide products (3) are described.
Journal ArticleDOI
Asymmetric Synthesis of α,α-Dibranched Amines by the Trimethylaluminum-Mediated 1,2-Addition of Organolithiums to tert-Butanesulfinyl Ketimines
Derek Cogan,Jonathan A. Ellman +1 more
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Asymmetric Synthesis of syn- and anti-1,3-Amino Alcohols
TL;DR: In this paper, the first application of metalloenamines derived from N-sulfinyl imines was reported for the highly diastereoselective addition to aldehydes.
Journal ArticleDOI
Synthesis, Utility, and Structure of Novel Bis(sulfinyl)imidoamidine Ligands for Asymmetric Lewis Acid Catalysis
Journal ArticleDOI
One-pot asymmetric synthesis of tert-butanesulfinyl-protected amines from ketones by the in situ reduction of tert-butanesulfinyl ketimines
TL;DR: In this paper, a one-pot method for the asymmetric synthesis of tert -butanesulfinyl-protected amines is described, where the ketones bd2 are condensed with (R)-tert -butaneulfinamide bd1 and the tert -Butaneulfinyl imine intermediates reduced in situ with NaBH 4 to afford the sulfinamides bd4 in 66% yield and with drs from 90:10 to 97:3 for both aryl alkyl and dialkyl ketones.