2-Pyridylsulfinamides as effective catalysts in the asymmetric alkylation of aldehydes with diethylzinc

Prasad, Kavirayani R.; Revu, Omkar

doi:10.1016/j.tet.2013.07.061

Cited by 18 publications

(6 citation statements)

References 29 publications

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“…To confirm the presence of a carbocation intermediate in this transformation, chiral alcohol ( S )‐1‐(4‐methoxyphenyl)propan‐1‐ol ( 13 )37a was subjected to the optimal reaction conditions. As expected, azide 14 was formed in 87 % yield as a racemic mixture (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Copper‐Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source

2015

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A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3‐dichloro‐5,6‐dicyano‐p‐benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation of ω‐halo azides and the azidation of allylic alcohols in the presence of a benzyl alcohol moiety. In addition, this strategy provides an opportunity to synthesize azides that can serve as precursors to β‐amino acids.

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Section: Resultsmentioning

confidence: 99%

Copper‐Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source

2015

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“…Colorless oil (151 mg, 98% yield); 97% ee value was determined by Chiral GC Chirasil Dex CB [Inlet temperature: 130 °C, t R = 11.83 min (major, R ), t R = 12.88 min (minor, S )]. [α] D 31.1 +37.0 ( c 1.00, CHCl 3 ) [Literature [α] D 24 −40.6 ( c 0.67, CHCl 3 ) for 90% ee ( S )]; 1 H NMR (400 MHz, CDCl 3 ): δ 0.87 (t, J = 7.5 Hz, 3H), 1.55–1.85 (m, 2H), 2.80 (br s, 1H), 4.51 (t, J = 6.6 Hz, 1H), 6.91–7.06 (m, 2H), 7.15–7.34 (m, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 10.0 (d, J = 27.4 Hz), 31.9, 75.2, 115.1 (d, J = 21.0 Hz), 127.6 (d, J = 8.1 Hz), 140.3 (d, J = 2.7 Hz), 162.1 (d, J = 243 Hz); 19 F NMR (376 MHz, CDCl 3 ): δ −115.4 (s, 1F).…”

Section: Experimental Sectionmentioning

confidence: 99%

“…(m, 2H), 7.35−7.53 (m, 2H);13 C NMR (100 MHz, CDCl 3 ): δ 72.2 (q, J = 32.2 Hz), 115.6 (d, J = 21.9 Hz), 124.1 (q, J = 282.1 Hz), 129.3 (d, J = 8.2 Hz), 129.7 (d, J = 1.7 Hz), 163.4 (d, J = 248.9 Hz);19 F NMR (376 MHz, CDCl 3 ): δ −78.6 (d, J = 6.7 Hz, 3F), −112.4 (m, 1F). (R)-1-(4-Fluorophenyl)propan-1-ol (4f) 55. Colorless oil (151 mg, 98% yield); 97%ee value was determined by Chiral GC Chirasil Dex CB [Inlet temperature: 130 °C, t R = 11.83 min (major, R), t R = 12.88 min (minor, S)].…”

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confidence: 99%

Chemo- and Enantioselective Addition and β-Hydrogen Transfer Reduction of Carbonyl Compounds with Diethylzinc Reagent in One Pot Catalyzed by a Single Chiral Organometallic Catalyst

et al. 2015

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Using a single chiral phosphoramide-Zn(II) complex as the catalyst, the asymmetric β-H transfer reduction of aromatic α-trifluoromethyl ketones and enantioselective addition of aromatic aldehydes with Et2Zn in one pot were successfully realized, affording the corresponding additive products of secondary alcohols in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee) and the reduction products of α-trifluoromethyl alcohols in good to excellent yields with up to 77% ee.

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“…The aq phase was extracted with EtOAc (3 × 5 mL) and the combined organic phase dried over anhydrous Na 2 SO 4 . The solvent was removed under reduced pressure and the product 12,14 was isolated by filtration through a short-path silica gel column using CHCl 3 (dried over CaCl 2 ) as the eluent. The enantiomeric excess was determined by GC analysis using a Supelco cyclodextrin β-DEX 120 capillary column (20 m x 0.25 mm I.D.…”

Section: Catalytic Asymmetric Addition Of Diethylzinc To Aldehydes; Gmentioning

confidence: 99%

Novel (+)-3-Carene Derivatives and Their Application in Asymmetric Synthesis

et al. 2014

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A simple synthetic procedure for the preparation of mono-N-tosylated-1,2-diamines derived from (+)-3-carene is described. (+)-3-Carene is transformed into the corresponding N-tosylaziridine derivative using chloramine-T trihydrate. Subsequent ring opening with sodium azide followed by reduction of the azide function gives the optically pure mono-N-tosylated-1,2-diamine. This ligand is effective in asymmetric transfer hydrogenations of aromatic ketones. It can also be transformed into other chiral ligands by alkylation of the amino group for application in the addition of diethylzinc to benzaldehydes.

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2-Pyridylsulfinamides as effective catalysts in the asymmetric alkylation of aldehydes with diethylzinc

Cited by 18 publications

References 29 publications

Copper‐Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source

Copper‐Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source

Chemo- and Enantioselective Addition and β-Hydrogen Transfer Reduction of Carbonyl Compounds with Diethylzinc Reagent in One Pot Catalyzed by a Single Chiral Organometallic Catalyst

Novel (+)-3-Carene Derivatives and Their Application in Asymmetric Synthesis

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