TCIメール No.123 | 東京化成工業
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- ありおき かみいしづ
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1 Mitsunobu A A ew Mitsunobu eagents C C C C TMAD ADDP C PBu3 C P3 CMMP CMBP
2 DEAD TPP A Et C C Et Et C C Et 2 A A ex. ucleophiles (A) P 3 P 3 1 xygen itrogen Carbon Sulfur C 3 C C S Ts Tf Scheme 1. TPP DEAD TPP DEAD redox condensation Walden Bz Tf DEAD-TPP 87% Tf Bz Scheme 2. 2
3 pk a pk a (i) pk a < 11 Et (ii) 11 < pk a < 13 (pk a = 8.3) DEAD-TPP 91% Et Ts (pk a = 11.7) DEAD-TPP 51% Ts (iii) pk a > 13 Et Et (pk a = 13.3) DEAD-TPP 0% Et Et Scheme 3. path a Et C C Et P 3 Et desired reaction Et Et (path a) side reaction (path b) 3 P 3 Et Et 4 Et 4 A P 3 A P A 1 2 A Et C C Et 6 2 Scheme 4. 3
4 A A path b pk a A DEAD,,','-tetraisopropylazodicarboxamide TIPA 1,1'-(azodicarbonyl)dipiperidine ADDP,,','-tetramethylazodicarboxamide TMAD C C TIPA Et Et 4 7 C C ADDP δ ' ' 2 ' δ C C TMAD DTD Scheme 5. 1,6-dimethyl-1,5,7-hexahydro-1,4,6,7-tetrazocin-2,5-dione DTD DEAD TBP Bu 3 P PBu 3 PBu 3 PBu Scheme 6. DEAD Ts 10 (pk a = 11.7) (1.5 equiv.) C C - PBu 3 (1.5 equiv.) 100 C, 24 h Ar, dry in sealed tube 62% Ts Scheme 7. 4
5 ' C P 3 C ' ' C C ' 2 P 3 ' C " P 3 X C P 3 X C P Ylide osphorane Scheme 8. A A A-' X C 3 X P 3 A ' P 3 A ' A ' P 3 Scheme 9. (cyanomethylene)tributylphosphorane CMBP (cyanomethylene)trimethylphosphorane CMMP CMMP C PBu 3 C P 3 (cyanomethylene)tributylphosphorane (cyanomethylene)trimethylphosphorane ( CMBP ) ( CMMP ) Scheme 10. DEAD 5
6 DEAD DEAD C C C C C C 17 Scheme 11. CMBP CMMP CMBP CMMP mmol T Wittig CMMP A C P' 3 A C 3 C P' 3 CMBP: = Bu CMMP: = Scheme 12. 6
7 S 2 ' 1) Base 2) ''-X S 2 ' '' ' '' Scheme 13. pk a pk a pk a DEAD pk a TIPA ADDP TMAD DTD CMBP CMMP CMBP CMMP Table 1. eaction of -thyl-p-tosylamide (10). % yield - DEAD-TPP *) Ts 10 (1.5 equiv.) (pk a = 11.7) edox system (1.5 equiv.), temp., 24 h edox system temp. TIPA-TBP ADDP-TBP TMAD-TBP DTD-TBP CMBP r.t. r.t. r.t. r.t. r.t. r.t. 100 C Ts CMMP r.t. 80 C *) The reaction was carried out in T. pk a Ts 2 P 3 DEAD Ts P 3 18 T, 0 C 98% 19 Scheme 14. 7
8 , CMMP CMBP Table 2. eaction of p-tosylamide (18). 18 (1.5 eq) CMBP (1.5 equiv.), temp., 24 h Ts (Ts 2 ) r.t. 80 C yield (%) yield (%) 93 a) (22) 85 (12) a) : no experimental result pk a pk a pk a pk a C C 20 (pk a = 11.2) 51% C C Et 21 (pk a = 10.7) 42% Et Et Et Et 22 (pk a = 13.3) 0% Scheme 15. Et Et 8
9 pk a DTD CMBP DTD DTD CMBP CMMP CMMP CMMP CMMP cis Table 3. eaction of enylsulfonylacetonitrile (23). S 2 C edox system (1.5equiv.), temp., 24 h S 2 C C S 2 % yield 23 (pk a = 12.0) (1.5 equiv.) edox system DEAD-TPP TMAD-TBP DTD-TBP CMBP r.t. r.t. r.t. r.t. 100 C 120 C CMMP 100 C 57 (22) 59 (3) 46 (51) 75 (21) 72 (28) 1) 64 (16) 52 (22) ex ) : no experimental result. S 2 C CMMP (1.5 equiv.), 100 C, 24 h S 2 C 26 (1.5 equiv.) 85% 23 (1.5 equiv.) CMMP (3 equiv.), 100 C, 24 h C S % Scheme 16. 9
10 pk a pk a MT pk a CMBP CMMP Table 4. eaction of MT Sulfone (28). S S 2 Tol edox system (1.5equiv.), temp., 24 h S S 2 Tol 28 (pk a = 23.4) % yield (1.5 equiv.) edox system TMAD-TBP r.t. DTD-TBP r.t. r.t. CMBP 100 C 120 C 150 C CMMP 100 C ) 40 2) 41 1) < ex 1) : no experimental result <1 2 2) 56 2) ) Dimeric ether was obtained pk a S 2 (1.5 equiv.) (pk a = 23.4) CMMP (1.5 equiv.) T, 80 C, 24 h S 2 90% C (1.5 equiv.) (pk a = 18.5) S 2 ex CMMP (3.0 equiv.) T, 80 C, 24 h 100% C ex S 2 S 2 (1.5 equiv.) (pk a = 16.7) ex CMMP (1.5 equiv.) T, 120 C, 24 h 100% ex S 2 Scheme
11 pk a CMMP (1.5 equiv.) S 2 CMMP (1.5 equiv.) DME, 100 C, 24 h 100% Bu S 2 CMMP (1.5 equiv.) ex ex DME, 120 C, 24 h S 2 76% Scheme 18. Walden pk a pk a C C ' DEAD-TPP ' or ' Scheme 19. pk a C Bz 29 DEAD-TPP 27% C DEAD-TPP no reaction 30 Scheme
12 TMAD p p p pk a p DEAD TMAD p DEAD 29 C TMAD-TBP (1.5 equiv.) 0 C, 10 min, then 60 C, 24 h = - : 98% (31 / 32 > 99.5 / 0.5) = 2 - : 28% (31 / 32 = 45 / 55) Scheme C TMAD-TBP (1.5 equiv.) 0 C, 10 min, then 60 C, 24 h 39% Scheme 22. Prashad CMBP 18 (2 equiv.) CMBP (3 equiv.), r.t. 71% Ts (1 equiv.) CMBP (1.5 equiv.), r.t. (1 equiv.) CMBP (1.5 equiv.), 100 C 71% Ts Scheme
13 Walden S C % ee 23 CMBP 120 C, 24 h, 79% S 2 C 6 13 C C 6 13 C >95% ee C C C % ee TolS 28 2 S CMBP C C C, 24 h, 98% ee 71% Scheme 24. C TBS S 2 12 CMMP (1.5 equiv.) T, 100 C, 24 h 91% S 2 TBS 11 Ts TMAD-PBu 3 S 2 11, r.t., 24 h 100% 11 Theonelladine D S 2 Ts 11 TMAD-PBu 3 Tol., r.t. 84% Theonelladine C 2 11 Scheme 25. norfaranal norfaranal anti S S 13
14 MPM 23 CMMP Tol., 100 C, 24 h 79% MPM C S 2 1) DEAD-P 3, C S 2 CMMP 2) 1 a, ex. / (1 / 3) 98% 100 C, 24 h 54% S 2 norfaranal Scheme S 1) Bn, TMAD-TPP, C 2 Cl 2 2) S, K 2 C 3, DM > 95% Bn S 2 1) Bn, TMAD-TBP, T 2) 95% TA / water high yield S 2 2 Scheme 27. staff SUB GAT 14
15 1). Mitsunobu, Synthesis, 1981, 1. 2) D. L. ughes, The Mitsunobu eaction. rganic eactions, Vol. 42, eds. by P. Beak, et al., John Wiley & Sons, Inc., ew York, 1992, p ) M. L. Edwards, D. M. Stemerick, J.. McCarthy, Tetrahedron Lett., 31, 3417 (1990). 4) M. Wada,. Mitsunobu, Tetrahedron Lett., 13, 1279 (1972). 5) S. Itô, T. Tsunoda, Pure & Appl. Chem., 71, 1053 (1999). 6),,, 52, 113 (1994). 7) T. Tsunoda, Y. Yamamiya, S. Itô, Tetrahedron Lett., 34, 1639 (1993). 8) T. Tsunoda, J. tsuka, Y. Yamamiya, S. Itô, Chem. Lett., 1994, ) T. Tsunoda,. Kaku,,,','-Tetramethylazodicarboxamide. Electronic Encyclopedia of eagents for rganic Synthesis eds. by L. A. Paquette, et al., Wiley, 15 ctober ) T. Tsunoda, M. agaku, C. agino, Y. Kawamura,. zaki,. ioki, S. Itô, Tetrahedron Lett., 36, 2531 (1995). 11) T. Tsunoda,. zaki, S. Itô, Tetrahedron Lett., 35, 5081 (1994). 12) T. Tsunoda, C. agino, M. guri, S. Itô, Tetrahedron Lett., 37, 2459 (1996). 13) I. Sakamoto,. Kaku, T. Tsunoda, Chem. arm. Bull., 51, 474 (2003). 14) T. Tsunoda,. Takagi, D. Takaba,. Kaku, S. Itô, Tetrahedron Lett., 41, 235 (2000). 15) J.. enry, L.. Marcin, M. C. McIntosh, P. M. Scola, G. D. arris, Jr., S. M. Weinreb, Tetrahedron Lett., 30, 5709 (1989). 16) G. Dauphin, A. Kergomard, Bull. Soc. Chim. r., 1961, ) S. Bittner, Y. Assaf, P. Krief, M. Pomerantz, B. T. Ziemnicka, C. G. Smith, J. rg. Chem., 50, 1712 (1985). 18) T. Tsunoda,. Yamamoto, K. Goda, S. Itô, Tetrahedron Lett., 37, 2457 (1996). 19) S. Ji, L. B. Gortler, A. Waring, A. Battisti, S. Bank, W. D. Closson, P. Wriede, J. Am. Chem. Soc., 89, 5311 (1967); J. Kovacs, U.. Ghatak, J. rg. Chem., 31, 119 (1966); E.. Gold, E. Babad, J. rg. Chem., 37, 2208 (1972); E. Vedejs, S. Lin, J. rg. Chem., 59, 1602 (1994). 20) T. Tsunoda, K. Uemoto, T. htani,. Kaku, S. Itô, Tetrahedron Lett., 40, 7359 (1999). 21) K. Uemoto, A. Kawahito,. Matsushita, I. Sakamoto,. Kaku, T. Tsunoda, Tetrahedron Lett., 42, 905 (2001). 22) S.. Martin, J. A. Dodge, Tetrahedron Lett., 32, 3017 (1991); J. A. Dodge, J. I. Trujillo, M. Presnell, J. rg. Chem., 59, 234 (1994). 23). Loibner, E. Zbiral, elv. Chim. Acta, 60, 417 (1977). 24) M. Saïah, M. Bessodes, K. Antonakis, Tetrahedron Lett., 33, 4317 (1992). 25) T. Tsunoda, Y. Yamamiya, Y. Kawamura, S. Itô, Tetrahedron Lett., 36, 2529 (1995). 26) M. Prashad,. J. Kathawala, T. Scallen, J. d. Chem., 36, 1501 (1993). 27) T. Suzuki, J. zaki,. Sugawara, Agric. Biol. Chem., 47, 869 (1983). 28) E. edenström,.-e. ögberg, A.-B. Wassgren, G. Bergström, J. Löfqvist, B. ansson,. Anderbrant, Tetrahedron, 48, 3139 (1992). 29) J. Kobayashi, T. Murayama, Y. hizumi, T. Sasaki, T. hta, S. ozoe, Tetrahedron Lett., 30, 4833 (1989). 30) K. Mori,. Ueda, Tetrahedron Lett., 22, 461 (1981); K. Mori,. Ueda, Tetrahedron, 38, 1227 (1983); L. Poppe, L. ovák, P. Kolonits, Á. Bata, C. Szántay, Tetrahedron, 44, 1477 (1988). 31) S.. Chhabra, A. Mahajan, W. C. Chan, J. rg. Chem., 67, 4017 (2002). 32) J. J. Scicinski, M. D. Barker, P. J. Murrary, E. M. Jarvie, Bioorg. d. Chem. Lett., 8, 3609 (1998). 15
16 IUPAC IUPAC C C C C C PBu 3 16
17 1b, Cu(Cl 4 ) b) 2 3 = =C 3 =C 2 Et Temp Y (%) endo/exo endo (% ee) >99 : 1 98 (2S) 95 : 5 99 (2S) 92 : 8 92 (2) 1 Cu(Cl 4 ) Cu(Tf) 2 i(cl 4 ) 2 1b Cu(Cl 4 ) Diels- Alder 3 1b) 1 Diels-Alder 2a) 2b) 2c) 2d) 1 3) 1) Diels-Alder catalysis with a bis(oxazoline) complex a) I. W. Davies, L. Gerena, D. Cai,. D. Larsen, T.. Verhoeven, P. J. eider, Tetrahedron Lett., 38, 1145 (1997). b) A. K. Ghosh,. Cho, J. Cappiello, Tetrahedron : Asymmetry, 9, 3687 (1998). 2) Applications in catalytic reaction of bis(oxazoline) complexes a) T. Saito, K. Takekawa, T. Takahashi, Chem. Commun., 1999, b). A. Porter,. eng, I. K. Kavrakova, Tetrahedron Lett., 40, 6713 (1999). c) X. Zhang, M. Ma, J. Wang, Tetrahedron : Asymmetry, 14, 891 (2003). d) M. Jiang, S. Dalgarno, C. A. Kilner, M. A. alcrow, T. P. Kee, Polyhedron, 20, 2151 (2001). 3) Enantioselective conjugate addition a) D. M. Barnes, et al., J. Am. Chem. Soc., 124, (2002). * * = i Pr (,) B2217 1g 16, mg 5,950 (S,S) B mg 8,400 1 = (,) B2219 1g 32, mg 10,500 (S,S) B mg 10,500 2 = t Bu (S,S) I0567 1g 44, mg 8,050 2 = (,) D2823 1g 20, mg 7,550 (S,S) I0582 1g 22, mg 8,250 2 * * 2 17
18 ø Tf Tf a) 1 pka=1.5 (in CD 3 C 2 D) Tf Tf 1 (3 mol%) Bz 2 (1.5 eq.) C 3 C, r.t., <1 h Bz i-pr i-pr Y. >99% 2 1a) 2 (0.1 mol%) () 3 C (1.2 eq.) toluene, 0 C, 1-2 h Y. >99% 2 1b) % M PLC GC 18
19 2 C Si 3 toluene (0.2 ml / min) Si 3 T : 2 (5 : 1) (0.2 ml / min) Y. 96% 1 1,1 1a 1c) 1a 1a 1a 1a 2 1a C 3 (C 2 ) 12 C 2 a Tf Tf Li 4 M Cl C 3 (C 2 ) 12 C 2 1a Tf Tf 1a (1 mol%) C Cyclohexane azeotropic reflux, 3 h Y. 86% 1a cyclohexane flask 1a, r.t.,, r.t. 1a 96% (cont.) 19
20 (cont.) 1 [C 6 5 CTf 2 ]Si 3 1b 1d) 1 Tf Tf 2 Tf > Tf 2 > 1 1b > Tf 2 Si 3 > TfSi b (0.5 mol%) methallyltrimethylsilane (2 mol%) heptane azeotropic reflux 3 Y. 89%, Purity 98% 1) Pentafluorophenylbis(triflyl)methane as a strong brønsted acid catalyst a) K. Ishihara, A. asegawa,. Yamamoto, Angew. Chem. Int. Ed., 40, 4077 (2001). b) K. Ishihara, A. asegawa,. Yamamoto, Synlett, 2002, c) K. Ishihara, A. asegawa,. Yamamoto, Synlett, 2002, d) A. asegawa, K. Ishihara,. Yamamoto, Angew. Chem. Int. Ed., 42, 5731 (2003). e),,, 115, 2 (2002). (CCl) 2 C, C 2 PS 1 C 3 PS Cl Cl C 3 2 Entry t Bu (C 2 ) 2 (C 2 ) 2 (C 2 ) 2 2 (C 2 ) 3 t Bu t Bu t Bu Yield (%) a 81 b 1 C 2, 2Cl 1 C, 2 condition: 2 (1.5 eq.), Et 3 (3 eq.), C 2 Cl 2, r.t., 48 h a Used a recycled polymer from entry 2 b Used a recycled polymer from entry tert 1 Polymer-supported DMI as a potential heterogeneous dehydrating agent W. Disadee, T. Watanabe, T. Ishikawa, Synlett, 2003,
21 Ultraviolet Light Visible Light or Dark (C 2 ) 2 colorless 1 2 Acid Visible Light in Acetonitrile (C 2 ) 2 2 Base Acid (C 2 ) 2 2 purple yellow-green 1 p 1) Molecular switch. M. aymo, S. Giordani, J. Am. Chem. Soc., 123, 4651 (2001).. M. aymo, S. Giordani, Proc. atl. Acad. Sci. U. S. A., 99, 4941 (2002). S. Giordani,. M. aymo, rg. Lett., 5, 3559 (2003). S VC Mixture Standard Solution (each 0.5 mg/ml in thanol) 1ml 2,750 S VC Mixture Standard Solution (each 0.5 mg/ml in thanol) 1ml 2,550 tert S VC Mixture Standard Solution (each 0.5 mg/ml in thanol) 1ml 2,950 S0676 tert-butyl thyl Ether (1 mg/ml in thanol) 1ml 1,300, eagent Guide 4 21
22 a Sm x 2 1a : 1 =, 2 = C 3 1b : 1 = C 3, 2 = M (Eu-pdta) α α M M Sm-pdta 1 M α α M Mosher 3 C 2 C C C 2 β 3 C γ α Valine ig M spectra (400 Mz) of valine (0.06 M, [D]/[L] = 1/2.85) in D 2 at p αpka p ~ 1 p ad M p D L M 5~20 mol% M 22
23 1 M 400 Mz [valine] = 0.06 M D/L = 1/2.85 p 9.4 [1a] / [valine] = ~ D/L = 1/3.02 D/L D/L α Table 1. esolution of enantiomer signals of amino acids in the presence of 1a. [1a] [] p δ (ppm) α α α β β δ (hi) D D D L L L δ δ L -δ D δ L 1a L 1 δ D D 1a α α D L L α α α α relatively higher than 2 L-Amino acid relatively lower than 2 D-Amino acid ig. 2. elative position of proton signals of amino acid enantiomers in the presence of 1a. 1a 1b 1b 1a 1 M p p p 8 1a 1b K. Kabuto, Y. Sasaki, J. Chem. Soc., Chem. Commun., 1987, 670. A. Inamoto, K. gasawara, K. mata, K. Kabuto, Y. Sasaki, rg. Lett., 2, 3543 (2000). K. mata, K. orie, K. gasawara, K. Kabuto, Y. Sasaki, CD
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DEAD TPP A Et C C Et Et C C Et 2 A A ex. ucleophiles (A) P 3 P 3 1 xygen itrogen Carbon Sulfur C 3 S Ts Tf Scheme 1. TPP DEAD TPP DEAD redox condensation Walden Bz Tf DEAD-TPP 87% Tf Bz Scheme 2. pk a
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DS0 0/9/,.,,.,,,.,.,.0%,.%.,,,, Speculative Execution in Distributed Controllers for High-Level Synthesis Shimizu iho Ishiura Nagisa bstract: This article proposes a method of incorporating speculative
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Stereoelectronic Effect
node anti bonding M ( σ* ) A A : bonding M ( σ ) A: atomic orbital M: molecular orbital node anti bonding M filled orbital of molecular 1 M bonding M vacant orbital of molecular 2 LUM LUM (lowest unoccupied
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