Diastereoselective Pinacol Coupling Reactions of α-Ketoamides Mediated by SmI2: Synthesis of Enantiomerically PureR andS Quaternary Tartaric Acids

Kim, Sam Min; Byun, Il Suk; Kim, Yong Hae

doi:10.1002/(sici)1521-3757(20000218)112:4<744::aid-ange744>3.0.co;2-7

Angewandte Chemie

2000

DOI: 10.1002/(sici)1521-3757(20000218)112:4<744::aid-ange744>3.0.co;2-7

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Diastereoselective Pinacol Coupling Reactions of α-Ketoamides Mediated by SmI2: Synthesis of Enantiomerically PureR andS Quaternary Tartaric Acids

Sam Min Kim¹,

Il Suk Byun²,

Yong Hae Kim³

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Cited by 11 publications

References 70 publications

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Samarium-Catalyzed Tandem Semipinacol Rearrangement/Tishchenko Reaction ofα-Hydroxy Epoxides: A Novel Approach to Highly Stereoselective Construction of 2-Quaternary 1,3-Diol Units

Fan

Wang

et al. 2001

Angew. Chem.

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Diastereoselective constructions of 1,3-diol units have always been in high demand in synthetic organic chemistry, and preparation of 2-quaternary 1,3-diol units is of major importantance for the synthesis of many biologically significant molecules, such as the Furaquinocins, [1] and chiral ligands. [2] However, the quaternary carbon atom is generally difficult to construct with high diastereoselectivity, because a simple aldol reaction of carbonyl compounds is not efficient in this situation. Several procedures for construction of 2-quaternary 1,3-diol units have already been developed on the basis of the Lewis acid mediated semipinacol rearrangement of a-hydroxy epoxides. However, they generally need one equivalent or an excess of a promoter and produce only the b-sum of the squares of the differences. The rate constants obtained in this way were multiplied by two. [14] Figure 3. a) 1D 1 H-{ 31 P} EXSY NMR spectrum recorded in CDCl 3 at 301 K on a sample containing 1, p-H 2 , and a 100-fold excess of diphenylacetylene. The resonance for 3t was selectively excited and the results for a reaction time of 700 ms are displayed. Exchange into 3b, 9, and cis-stilbene is indicated; b) 2D 1 H-{ 31 P} EXSY spectrum (positive contours) of an identical sample employing a mixing time of 400 ms. Off-diagonal peaks arise due to chemical exchange.

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Samarium-Catalyzed Tandem Semipinacol Rearrangement/Tishchenko Reaction ofα-Hydroxy Epoxides: A Novel Approach to Highly Stereoselective Construction of 2-Quaternary 1,3-Diol Units

Fan

Wang

et al. 2001

Angew. Chem.

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show abstract

Samarium-Catalyzed Tandem Semipinacol Rearrangement/Tishchenko Reaction ofα-Hydroxy Epoxides: A Novel Approach to Highly Stereoselective Construction of 2-Quaternary 1,3-Diol Units

Fan

Wang

et al. 2001

Angew. Chem. Int. Ed.

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Visible Light‐Mediated Copper(I)‐Catalysed Aerobic Oxidation of Ynamides/Ynamines at Room Temperature: A Sustainable Approach to the Synthesis of α‐Ketoimides/α‐Ketoamides

2017

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An ovelv isible light-mediated, coppercatalysed aerobic oxidation of the C Cb ond in ynamides/ynamines at room temperature by using molecular oxygen as an oxidanti sd escribed. Overall, 23 examples were demonstrated with substrates having aw ide range of functional groups.T he current protocolc an be readily scaled up to ap reparative (1-2 g) scale with high yields (78-92%), high atom efficiency,a nd reactionm ass efficiency.T he mechanistic studys howst hat in-situ formation of ac opper(I)-coordinated p-complex (l max = 460 nm) is most probably the key light absorbing species responsible for the visible light-induced oxidation of ynamides and ynamines.T his sustainableo xidation approach allowst he direct synthesiso fp otentially importantnovel a-ketoimide/a-ketoamide skeletons without the need of external oxidants (organic/inorganic oxidants) andg eneration of stoichiometric amounts of wastes.

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Diastereoselective Pinacol Coupling Reactions of α-Ketoamides Mediated by SmI2: Synthesis of Enantiomerically PureR andS Quaternary Tartaric Acids

Cited by 11 publications

References 70 publications

Samarium-Catalyzed Tandem Semipinacol Rearrangement/Tishchenko Reaction ofα-Hydroxy Epoxides: A Novel Approach to Highly Stereoselective Construction of 2-Quaternary 1,3-Diol Units

Samarium-Catalyzed Tandem Semipinacol Rearrangement/Tishchenko Reaction ofα-Hydroxy Epoxides: A Novel Approach to Highly Stereoselective Construction of 2-Quaternary 1,3-Diol Units

Samarium-Catalyzed Tandem Semipinacol Rearrangement/Tishchenko Reaction ofα-Hydroxy Epoxides: A Novel Approach to Highly Stereoselective Construction of 2-Quaternary 1,3-Diol Units

Visible Light‐Mediated Copper(I)‐Catalysed Aerobic Oxidation of Ynamides/Ynamines at Room Temperature: A Sustainable Approach to the Synthesis of α‐Ketoimides/α‐Ketoamides

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