Guanidine and guanidinium salt catalyzed enantioselective phosphorus carbon bond formation reactions 2

... CH2 Cl2 , -20 o C O 93a 122 H S O N O Ph 124 80% yield, 99% ee OH O OH OH R1 R2 122 MeOC O R2 124 OH H CO2 Me 124 a 92% yield 98% ee OH PhOC OH 114a (10 mol%) CH 2Cl2, -20 oC OH O O OH H CO2 Et ... (99%) 103d : R1=Ph; R 2= CN (97%) 103e : R 1=Ph; R2 =COPh (80%) 102a : R 1=R 2= CN 102b: R1=R2 =CO 2Me 102c: R 1=R 2= COPh 102d : R1=Ph; R 2= CN 102e : R 1=Ph; R2 =COPh O O Ph2 P(O)H TBD Ph Ph...

Ngày tải lên: 14/09/2015, 08:38

... Ph2CH 90 R /S 3 :1 86 :1 5 :1 55 :1 12 :1 54 :1 Scheme 1. 11 Ebetino’s asymmetric Michael addition of phosphinic and aminophosphinic acid An asymmetric Michael addition of phosphinic and aminophosphinic ... Adv Synth Catal 2004, 346, 10 35 10 50 Hiratake, J.; Oda, J., Biosci Biotech Biochem 19 97, 61, 211 – 218 Pietrusiewicz, K M.; Zablocka, M., Chem Rev 19 94, 94, 13 75 14 11...

Ngày tải lên: 14/09/2015, 08:38

... Chapter 181a 56 30 ; 25 136 b [2-NpCH2] 181b 37 35 ; 15 136 c [3, 5-MeOC6H4CH2] 181c 58 32 ; 20 136 d [3- NO2C6H4CH2] 181d 58 36 ; 14 136 e [Et] 181e 45 38 ; 18 a 136 a [Bn] 136 f [i-Bu] 181f 48 56; 32 donor : ... 1:11 tBu F3 C F3C H N H N Ph Ph NH Ph CF3 CF3 BAr F-4 = B HN 2BAr F-4 Ph F3C CF3 F3 C 148 CF3 Scheme 3. 1 Göbel’s chiral bis(amidinium) salt 148 catalyzed Diels-Alder re...

Ngày tải lên: 14/09/2015, 08:38

... - 34. 8 IR (KBr) 7 74, 15 04, 3050 cm-1 HRMS (ESI) m/z 44 0.1 348 (M+H+), calc for C28H24ClNP 44 0.1335 The ee of 147 was determined by converting back to 146 using H2O2 4. 6 Protocol for guanidinium salt ... 127.2, 127.3, 127 .4, 127.6, 127.9, 128.0, 129.3, 129.6, 129.7, 130.3, 132.9, 133.0, 133.3, 133 .4, 133.9, 1 34. 0, 1 34. 1, 1 34. 2, 1 34. 3, 1 34. 6, 1 34. 7, 137.8, 139.9, 142...

Ngày tải lên: 14/09/2015, 08:38

... especially the design of novel chiral indium( III) complexes for catalytic enantioselective carbon- carbon bond formation and their application to the synthesis of bioactive molecules In this part of the ... growth of indium metal chemistry, various indium( III) complexes have gained widespread application as efficient Lewis acid catalysts for carbon- carbon b...

Ngày tải lên: 30/09/2015, 06:07

... the formation of a benzoylpalladium intermediate which either reacts with the alkynol or liberates benzoic acid; hence the formation of considerable amounts of the latter Carbon-carbon bond formation ... is of great interest Carbon-carbon bond formation 221 Aqueous palladium-catalyzed Sonogashira coupling reactions were also applied for the preparation of polymers (see Chapte...

Ngày tải lên: 23/12/2013, 07:19

... 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...

Ngày tải lên: 10/09/2015, 15:51

... 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,...

Ngày tải lên: 14/09/2015, 14:12

... GUANIDINE CATALYZED ENANTIOSELECTIVE MANNICH REACTION: TOWARDS THE SYNTHESIS OF  -AMINO ACIDS PAN YUANHANG (BSc., Zhejiang University) A THESIS SUBMITTED FOR THE DEGREE OF DOCTOR OF PHILOSOPHY ... the enantioselecitive decarboxylative Mannich and amination reactions of MAHTs catalyzed by bicyclic guanidine in the following chapters The mechanistic stud...

Ngày tải lên: 10/09/2015, 08:31

... BICYCLIC GUANIDINE CATALYZED ENANTIOSELECTIVE ISOMERIZATION REACTIONS LIU HONGJUN 2010 BICYCLIC GUANIDINE CATALYZED ENANTIOSELECTIVE ISOMERIZATION REACTIONS LIU HONGJUN ... this study is to develop highly enantioselective isomerization reactions catalyzed by chiral bicyclic guanidines A chiral bicyclic guanidine was found to catalyze the isomerization o...

Ngày tải lên: 11/09/2015, 09:17

... and co-workers Scheme 1. 5 Proposed mechanism of gadolinium -catalyzed desymmetrization of meso- aziridines with TMSCN Scheme 1. 6 Gadolinium -catalyzed desymmetrization of meso- aziridines with TMSCN ... 1. 12 Chiral phosphoric acid -catalyzed desymmetrization of mesoaziridines with TMS-SPh developed by Della Sala and co-workers Scheme 1. 13 Chiral phosphoric acid...

Ngày tải lên: 11/09/2015, 10:05

... 79b 79c 79d 25 25 -20 -20 -20 -20 -20 -20 24 24 24 24 20 20 20 20 100 100 90 90 94d 94d 89d 92d 15 13 30 17 33 2 a All reactions were performed with 0. 02 mmol of aziridine, 0.04 mmol of thiol and ... racemization Scheme 2. 12 Chiral bicyclic guanidine catalyzed Diels-Alder reactions of anthrones .21 32 Chapter 2. 1 .2 Bicyclic guanidine catalyzed enantioselec...

Ngày tải lên: 11/09/2015, 10:05

... Structure of fluoxetine Scheme 3. 4 Synthesis of carbodithioic acid esters of fluoxetine 63 Chapter 3. 2 Guanidine catalyzed enantioselective desymmetrization of meso- aziridines with in situ generated ... Table 3. 3 Chiral guanidine 79b catalyzed desymmetrization of various meso N-acyl aziridines 12 with amine and CS2 a 12 (R =3, 5-dinitrobenzoyl) 96 x mol%...

Ngày tải lên: 11/09/2015, 10:05

... 148 .7, 162.1 FTIR (film): 928, 1 045 , 1216, 142 5, 1520, 1 643 , 2977, 3020, 344 6 cm-1 LRMS (ESI) m/z 44 2.1 (M-H+), HRMS (ESI) m/z 44 2.0 044 (M-H+), calc for C17H14Cl2N3O5S 44 2.0037 The enantiomeric excess ... 28.2, 28 .4, 54. 0, 57.6, 83.5, 84. 7, 128.1, 129 .4, 130.3, 130.9, 133 .4, 137.2, 141 .7, 144 .3, 168.1, 169.1 FTIR (film): 758, 928, 1 045 , 1159, 1216, 1 349 , 142 4, 1522,...

Ngày tải lên: 11/09/2015, 10:05

... 64.0, 124.3, 1 25. 6, 126.7, 127.7, 128 .5, 129 .5, 130 .5, 132 .5, 134 .5, 1 35. 5, 140.0, 1 65. 4, 189.3, 191.1 FTIR (film): 1020, 1182, 1228, 1271, 1 456 , 152 5, 16 45, 1692, 17 45, 2 856 , 2934, 3 057 cm-1 LRMS ... NMR ( 75 MHz, CDCl3, ppm): δ 14.4, 24.1, 49.4, 64.0, 1 25. 9, 128.7, 133.1, 137.3, 140.1, 153 .4, 1 65. 4, 189.6, 191.0 FTIR (film): 1016, 1 155 82, 1218, 1286, 1380, 1 452 ,...

Ngày tải lên: 11/09/2015, 10:05