Organocatalytic conjugate addition reactions
Alpha fluorinated aromatic ketone as nucleophile in asymmetric organocatalytic c n and c c bonds formation reactions 2
... deprotonation/deuteriation process 2. 2 Enantioselective H/D exchange of -fluorinated aromatic ketones 2. 2.1 Synthesis of -fluorinated aromatic cyclic ketones and chiral bicyclic guanidine catalyst ... much (entries 12- 13) Table 2. 1 Optimization of the asymmetric H/D exchange reaction of -fluorinated ketone 82a in different conditions (Scheme 2. 6) incorporation en...
Alpha fluorinated aromatic ketone as nucleophile in asymmetric organocatalytic c n and c c bonds formation reactions 4
... 3.7 Asymmetric amination reation of -fluorinated aromatic cyclic ketone Scheme 3.8 Other -fluorinated compounds tested in asymmetric amination a Conversion of corresponding products determined ... cyclic ketone nucleophiles in asymmetric amination reaction catalyzed by chiral bicyclic guanidine Under the optimal reaction conditions, the chiral -hydrozino- -fluorinated...
Alpha fluorinated aromatic ketone as nucleophile in asymmetric organocatalytic c n and c c bonds formation reactions 4a
... -fluorinated aromatic ketones in the asymmetric Mannich and Michael reactions 4.2 Asymmetric Mannich reaction of -fluorinated aromatic ketones 4.2.1 Synthesis of imines and pentanidines; Pentanidines ... Enatioselective C- C bond formation 4.1 Introduction Asymmetric C- C bond formation reactions are important reactions in organic synthesis Among the variou...
Alpha fluorinated aromatic ketone as nucleophile in asymmetric organocatalytic c n and c c bonds formation reactions 5
... 121 Experimental Colorless oil LRMS (ESI) m/z 55 1.3 (M+Na+); 5. 5 Protocol for bicyclic guanidine catalyzed asymmetric C- C bond formation reactions and characterization of products Procedures for ... 254 nm; retention time: major isomer: 124.3 min; minor isomer: 132.8 5. 4 Protocol for bicyclic guanidine catalyzed asymmetric C- N bond formation reaction and characteriza...
Alpha fluorinated aromatic ketone as nucleophile in asymmetric organocatalytic c n and c c bonds formation reactions
... asymmetric conjugated addition reactions Most aliphatic ketone and acetophenone nucleophiles used in organocatalytic asymmetric transformations rely on the formation of highly reactive enamine intermediates.1 ... basic phase-transfer conditions We will describe the asymmetric H/D exchange reaction, C- N and C- C bonds formation reactions catalyzed by our guanidin...
Asymmetric organocatalytic conjugate additions with vinyl sulfones
... Used in Conjugate Additions 15 1.5 Asymmetric Conjugate Adddition to Vinyl Sulfones 18 1.5.1 Enamine-Based Conjugate Additions to Vinyl Sulfones 18 1.5.2 Conjugate Addition to Vinyl Sulfones ... α-cyano vinyl sulfones 22 Scheme 1-20 Asymmetric conjugate additions of α-chloro aldehydes to vinyl sulfone 22 Scheme 1-21 Facial conversions to vinyl sulfone a...
Bicyclic guanidine catalyzed enantioselective allylic addition reactions
... BICYCLIC GUANIDINE CATALYZED ENANTIOSELECTIVE ALLYLIC ADDITION REACTIONS WANG JIANMIN 2011 BICYCLIC GUANIDINE CATALYZED ENANTIOSELECTIVE ALLYLIC ADDITION REACTIONS WANG JIANMIN ... develop highly enantioselective allylic addition reactions catalyzed by chiral bicyclic guanidines A chiral bicyclic guanidine was found to catalyze a direct asymmetric...
Organocatalytic reactions of 3 hydroxy 2 pyrone and n arylsulfonyl 3 hydroxy 2 pyridone 1
... 3- hydroxy- 2- pyrone and N- substituted- 3hydroxy- 2- pyridone Chapter References 10 11 12 13 14 Nicolaou, K C.; Snyder, S A.; Montagnon, T.; Vassilikogiannakis, G Angew Chem Int Ed 20 02, 41, 16 68 -16 98 ... 1. 1) .10 Enantiomeric excess as high as 77% was obtained and the selectivity was good H HO N R2 OR1 R N N R = H, cinchonidine R = OMe, quinine N H R1 = R2 =...
Organocatalytic reactions of 3 hydroxy 2 pyrone and n arylsulfonyl 3 hydroxy 2 pyridone 2
... 3( 0) 10 3a MeCN Ph rt 82 5(0) 11 3a CH2Cl2 Ph -20 80 81 (20 ) 12 3a CH2Cl2 Ph -40 82 85(15) 13 3a CH2Cl2 Ph -40 81 88 (28 ) 14 3a CH2Cl2 Cy -40 82 88 (20 ) 15 a CPS 3a CH2Cl2 Bn -40 83 87 (20 ) Isolated ... product of 3- hydroxy- 2- pyrone and 2- chloro-5-nitrobenzaldehyde was protected with TsCl in the presence of triethylamine using standard procedures Scheme 2. 22 Pro...
Enantioselective tandem conjugate addition elimination reactions 1
... Chapter 1. 1 Tandem conjugate addition- elimination (CA-E) reactions The SN2′ reaction (1) and the tandem conjugate addition- elimination reaction (2) which yields ... ee 11 K Fuji, M Node, H Nagasawa, Y Naniwa, T Taga, K Machida and G Snatzke, J Am Chem Soc., 19 89, 11 1, 79 21- 7925 12 R Tamura, K.-i Watabe, N Ono, Y Yamamoto, J Org Chem., 19 92, 57, 4895-4903 13 ......
Enantioselective tandem conjugate addition elimination reactions 2
... conditions 29 Chapter O O Br COR1 CH 3CN, rt + 1.5 eq 11h COR2 Entry 20 a-e 20 [R1, R2] 20 a[R1= R2= S COR R 2OC 21 a-e Product ] Time(hr) Yield/%a ee/%b 21 a 16 83 94 2c 20 a 21 a 21 74 94 3d 20 a 21 a 21 87 ... CH 2Cl2, rt 2eq Et 3N 29 a-k R O R P X P X R R SN2' type SN2 type Entry 29 , R X Time (hr) Yield%b Product 29 a, Ph O 17 SN2′ type 29 b, p-FPh O 23 SN2′ type 29 c,...
Enantioselective tandem conjugate addition elimination reactions 3
... 40a 96 - 67 3: 1 39 b, 4-NO2 40b 27 47 54 5:1 39 c, 4-CN 40c 21 64 39 5:1 39 d, 4-CF3 40d 97 82 38 3: 1 39 e, 4-Cl 40e 24 31 47 2:1 39 f, 2-Cl 40f 96 35 47 3: 1 39 g, 3- Cl 40g 44 36 60 4:1 39 h, 3- Br 40h ... 11 32 42d, OBn 43d 16 93 40 42e, OCHPh2 43e 27 49 45 42f, OnBu 43f 75 31 7 42g, OtBu 43g 68 20 38 42h, OCH2CF3 43h 12 43 42i, CH3 43i 27 22 46 10 42j, Et 43j 26 20...
Enantioselective tandem conjugate addition elimination reactions 4
... ee%b Entry R 4- NO2 Me 56a 10 90 50 2c 4- NO2 Me 56a 12 89 54 3d 4- NO2 n Bu 56b 14 50 41 4- NO2 Bn 56c 89 48 3-NO2 Bn 56d 73 47 2-NO2 Bn 56e 72 14 4-CN Bn 56f 63 48 2-Cl-5-NO2 Bn 56g 82 31 a Isolated ... 2002, 1 14, 46 89 -46 92; Angew Chem Int Ed., 2002, 41 , 45 07 -45 10 (d) M Shi and J.-K Jiang, Tetrahedron: Asymmetry, 2002, 13, 1 941 -1 947 (e) M Shi, Y.-M Xu and Y.-L Shi,...
Enantioselective tandem conjugate addition elimination reactions 5
... 2 157 -2163 1 15 Chapter 13 C NMR (50 0 MHz, CDCl3, ppm) δ 25. 5, 25. 6, 25. 7, 29.1, 29.2, 45. 5, 73.1, 121.2, 122 .5, 1 25. 8, 129.3, 132 .5, 144.1, 147.4, 206.3; IR (film, cm-1) 3413, 1020, 2934, 153 2; ... 1H, J = 5. 8 Hz), 5. 62 (d, 1H, J = 5. 8 Hz), 5. 99 (s, 1H), 6.22 (s, 1H), 7 .53 (d, 2H, J = 8.7 Hz), 8.18 (d, 2H, J = 8.7 Hz); 13C NMR (300 MHz, CDCl3, ppm) δ 25. 5, 25. 6, 25. 7,...
Organocatalytic conjugate addition reactions
... Michael reactions of hydroxycarbamates 156a with different Michael acceptors List of Figures Fig 1.1 Publications for asymmetric organocatalytic conjugate additions and organocatalytic reactions ... quaternary ammonium catalyzed conjugate addition Scheme 1.2 Mukaiyama’s chiral quaternary ammonium phenoxide catalyzed conjugate addition in a tandem Mukaiyama-Michael addition...
Từ khóa:
- carbonyl chemistry 1 addition reactions
- equilibrium in addition reactions
- other addition reactions additions of cyanide and bisulfite
- addition reactions of nitrogen base imine and enamine formation
- irreversible addition reactions a general synthesis of alcohols
- organobromine compounds in reactions of homolytic addition and telomerization
- chemical reactions