Application of New Camphor-Derived Mercapto Chiral Auxiliaries to the Synthesis of Optically Active Primary Amines

Yang, Teng‐Kuei; Chen, Ruey-Yuan; Lee, Dong‐Sheng; Peng, Wen-Shiuan; Jiang, Yaozhong; Mi, Aiqiao; Jong, Ting‐Ting

doi:10.1021/jo00083a037

Cited by 96 publications

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“…575 Nucleophilic additions to camphor-based sulfinyl imines were also found to be a useful method for the synthesis of chiral amines (Scheme 426). 576 Of all the nucleophiles examined, among the most stereoselective was allylmagnesium bromide. It was suggested that methylmagnesium iodide was behaving as a larger nucleophile by aggregation and that addition of allylmagnesium halides added by a mechanism involving allylic transposition, as observed for the other systems.…”

Section: Additions Of Allylmagnesium Reagents To Complexes Of Imines ...mentioning

confidence: 99%

Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin–Anh and Chelation-Control Models

et al. 2020

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This review describes the additions of allylmagnesium reagents to carbonyl compounds and to imines, focusing on the differences in reactivity between allylmagnesium halides and other Grignard reagents. In many cases, allylmagnesium reagents either react with low stereoselectivity when other Grignard reagents react with high selectivity, or allylmagnesium reagents react with the opposite stereoselectivity. This review collects hundreds of examples, discusses the origins of stereoselectivities or the lack of stereoselectivity, and evaluates why selectivity may not occur and when it will likely occur. CONTENTS 4.2.5. Additions to β-Substituted Aldehydes 4.2.6. Additions to Aldehydes with Distant Chelating Groups 4.3. Additions to Cyclic Ketones 4.3.1. Alkoxy-Substituted Cyclic Ketones 4.3.2. Additions to Alkoxy-Substituted Five-Membered-Ring Ketones 4.3.3. Additions to Alkoxy-Substituted Four-Membered-Ring Ketones 4.4. Additions of Allylmagnesium Halides to Cyclic Hemiacetals 5. Diastereoselectivity of Reactions of Allylmagnesium Reagents with Carbonyl Compounds by Felkin−Anh Control 5.1. Felkin−Anh Stereoselectivity 5.2. Additions to α-Chiral Acyclic Ketones 5.3. Additions to Chiral Exocyclic Ketones and Aldehydes 5.4. Additions of Allylmagnesium Halides to Chiral Cyclic Ketones Controlled by Felkin−Anh Selectivity 5.5. Additions of Allylmagnesium Halides to Chiral Acyclic Aldehydes 6. Diastereoselectivity of Reactions with Carbonyl Compounds by Steric Approach Control 6.1. Steric Approach Control and Stereoselectivity

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Section: Additions Of Allylmagnesium Reagents To Complexes Of Imines ...mentioning

confidence: 99%

Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin–Anh and Chelation-Control Models

et al. 2020

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“…According to results of previous researches, optically active sulfoxides of the terpene series were prepared by the oxidation of the corresponding sulfides using various oxidizing agents, including m- chloroperbenzoic acid (Binns et al, 1985 ; Annunziata et al, 1987 ; Eschler et al, 1988 ; Pyne et al, 1989 ; Arai et al, 1991 ), sodium periodate (Vargas-Díaz et al, 2005 ), air oxygen (Nikitina et al, 2001 ), as well as by the Kagan-Modena and Bolm asymmetric oxidation methods (Yang et al, 1994 ; Aversa et al, 2002 ; Demakova et al, 2012a , b ). We also reported that the crystal of the diastereomer 2a might be obtained as a result of the crystallization after a careful separation of the dimer crystals (Startseva et al, 2014 ).…”

Section: Resultsmentioning

confidence: 99%

Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example

et al. 2018

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In this article we present the synthesis of enantiomerically pure sulfoxide and study the influence of this compound on hemostasis. Detailed NMR studies and molecular dynamics simulations using sodium dodecyl sulfate (SDS) membrane models indicated that the bicyclic fragment of sulfoxide was embedded into the SDS micelle whereas the -SO(CH2)2OH fragment remained on the surface of the micelle and was in contact with the solvent. We also found that the pro-coagulative activity of sulfoxide was due to its ability to inhibit platelet activation and inhibited the catalytic activity of phospholipid surface which was involved in formation of coagulation clotting factor complexes.

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“…The mixture was extracted with ether (3 × 30 mL) and the combined organic phases were washed with brine (30 mL), dried (MgSO 4 ), and concentrated in vacuo. The residue was purified by chromatography (hexane-EtOAc, 6:1) to give 31 (277 mg, 87%) as a coloress oil: 16), 106 (7). Anal.…”

Section: -Methoxybenzaldehyde O-[(1s)-2-methoxy-1-phenylethyl]oxime (31)mentioning

confidence: 99%

“…Calcd for C 23 H 25 NO 4 : C, 72.80; H,6.64; N, 3.69. Found: Colorless oil: [α] 19 D +29.9 (c 0.3, CHCl 3 ); IR (neat) 3419 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 2.42 (1H, br s), 3.31 (3H, s), 3.58 (1H, A part of ABX, J = 12.1, 3.1 Hz), 3.71 (1H, B part of ABX, J = 12.1, 8.8 Hz), 4.84 (1H, dd, J = 8.8, 3.1 Hz), 5.12 (1H, 1/2 ABq, J = 6.7 Hz), 5.17 (1H, 1/2 ABq, J = 6.7 Hz), 5.70 (1H, s), 6.14 (br s), 7.05-7.37 (12H, m),7.55 (1H, d, J = 7.7 Hz), 7.66 (1H, d, J = 7.7 Hz); 13 C NMR (100.6 MHz, CDCl 3 ) δ 56.2 (CH 3 ), 63.1 (CH), 66.9 (CH 2 ), 85.9 (CH), 94.6 (CH 2 ), 114.3 (CH), 121.9 (CH), 126.9 (CH, 2 carbons),127.5 (CH), 128.0 (CH), 128.2 (CH, 2 carbons), 128.4 (CH, 2 carbons), 128.55 (CH, 2 carbons), 128.6 (CH), 129.8 (C), 138.6 (C), 140.0 (C), 154.7 (C); ESI m/z [M + H] + 380; HRMS (ESI) calcd for C 23 H 26 NO 4 [M + H] + 380.1862, found 380.1876. (1R)-1-Phenyl-2-({[(1S)-1-phenylethyl]amino}oxo)ethanol [(S,R)-21].…”

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Enantioselective Synthesis of Primary 1‐(Aryl)alkylamines by Nucleophilic 1,2‐Addition of Organolithium Reagents to Hydroxyoxime Ethers and Application to Asymmetric Synthesis of G‐Protein‐Coupled Receptor Ligands.

2004

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Ligands. -Oximes (I) and (VIII), both derived from methyl (R)-mandelate, are converted into diastereomerically enriched adducts by addition of organolithium compounds. After removal of the chiral auxiliary by N-O bond cleavage the latter give the desired (R)and (S)-amines. Both enantiomers of hydroxyphenyl(ethyl)amine (V), previously used as an efficient chiral auxiliary, are obtained by this method. The synthetic utility of the present method is further demonstrated by the synthesis of calcium receptor agonist NPS R-568 (VIc) and its thio analogue (VIh), and by transformation of vinyl derivative (R)-(IVg) into NK-1 receptor antagonists CP-99,994 and CP-122,721 (VII). -(ATOBE, M.; YAMAZAKI, N.; KIBAYASHI*, C.; J. Org. Chem. 69 (2004) 17, 5595-5607; Sch. Pharm., Univ. Pharm. Life Sci., Hachioji, Tokyo 192, Japan; Eng.) -Klein 51-068

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Application of New Camphor-Derived Mercapto Chiral Auxiliaries to the Synthesis of Optically Active Primary Amines

Cited by 96 publications

References 0 publications

Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin–Anh and Chelation-Control Models

Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin–Anh and Chelation-Control Models

Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example

Enantioselective Synthesis of Primary 1‐(Aryl)alkylamines by Nucleophilic 1,2‐Addition of Organolithium Reagents to Hydroxyoxime Ethers and Application to Asymmetric Synthesis of G‐Protein‐Coupled Receptor Ligands.

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