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1 ,'-bis(salicylidene)ethylenediamine Scheme n 5 5 5' 3 3' = stereogenic center 1 = bulky and/or chiral substituent Scheme 1.
2 ,,,, Fig. 1 stepped conformation 2 A achiral metallosalen complex (= ) enantiomeric and = achiral B (= ent-a) A B A B chiral metallosalen complex ( ) diastereomeric or = chiral umbrella conformation Fig. 1. Some conformers of metallosalens. C stepped A B umbrella C gauche A B eclipsed C = A B = ent-a A B,' Scheme (4 mol%) 4 (5 mol%) 2 Ac I C 2 Cl 2, -20 C Ac 82% ee, 65% t-bu n t-bu PF 6 t-bu t-bu 3 Scheme
3 - β Fig. 2 Zr u f β β β Λ β β α ( ) enantiomeric cis-β isomer (Λ) cis-α isomer Fig. 2. Structures of cis-isomers. C- Scheme 3 G=: P= non, = I G=: P=, = I or 2 G=C: P= and, = 2 PG P-G= GP S P G S G - P Scheme 3. eaction via oxenoid, nitrenoid, or carbenoid intermediate. Jacobsen Scheme 4
4 Scheme 3, G=, P= non 1 L 1 - Fig. 3-2 L s L Scheme s Jacobsen 3 5 n 3 1 L 1 3' 5' 2 Fig. 3. t t 4-PP Scheme 4 n(salen) I= or acl 4-PP 4-PP= 4-phenylpyridine -oxide : = V=, 1 = t-bu, 2 =, 3, 3 = -(C 2 ) 4 -, = non 6: = n, 1 = t-bu, 2 =, 3 =, = PF 6-7: = n, 1 = C(Et), 2 =, 3 =, = PF 6-8: = n, 1, 2 = t-bu, 3, 3 = -(C 2 ) 4 -, = Cl 6: 78% ee, 72% 8: 86% ee, 67% 9: 96% ee, 61% Ar Ar (S) n Ac () 9: Ar= 3,5-(C 3 ) 2 C 6 4 Scheme 4.
5 Scheme 5 10, hν, TP r.t. 82% ee TP= tetramethylpyrazine,'-dioxide 10, hν, DCP r.t. 87% ee DCP= 2,6-dichloropyridine -oxide (S) u Cl 10 () TP or - DCP u u u Cl hν Cl Cl 10 Scheme 5. epoxidation C- C-,S, 4-PP 11 (2 mol%), I -30 C, C 6 5 Cl 11 (2 mol%), I -30 C, C 6 5 Cl 89% ee 90% ee () n PF 6 11 () Scheme 6. p Scheme 7
6 Ar 12, C 3 C 6 4 S 2 =I rt, 4-PP Ar Ar= : 94% ee, 76% Ar= p-clc 6 4 : 86% ee, 70% Ts e e n Ac Scheme Che Scheme 8 13a (11 mol%) Ts Sie 3 I=Ts, C 2 Cl 2, r.t. 13b (11 mol%) I=Ts, C 2 Cl 2, r.t. 83% ee, 68% Ts 97% ee, 17% L= P L 3 u L Bu-t t-bu 13a: = 2, 13b: = Br Scheme 8. Ts 3 Jacobsen Ts 3 C Ts 3 S Ts C 3 14 (2 mol %) S C S 4A, C 3 Ts 2 Cl 2, r.t. 3 98% ee, 99% S C 3 14 (2 mol %) S C S 4A, C 3 2 Cl 2, r.t. Cl 3 CC(C 3 )C 3 95% ee, 93% = CC(C 3 ) 2 CCl 3 C u 14 Scheme 9.
7 14, Ts 3 S 4A, C 2 Cl 2, r.t. Ts 87% ee, 71% 14, Ts 3 S 4A, C 2 Cl 2, r.t. Ts 14, Ts 3 S 4A, C 2 Cl 2, r.t. Ts 92% ee, 25% Scheme % ee, 85% C- C- C- 15, I=Ts Ts S 4Å, -40 C, C 2 Cl 2 15, I=Ts S 4Å, -40 C, C 2 Cl 2 89% ee, 71% Ts Br n PF 6 Br 15 Br Br 77% ee, 67% Scheme 11. -Co 2 CC 2 -t-bu Co 16 C 2 -t-bu 16 C 2 Cl 2, r.t. trans cis trans : cis = I, = t-bu: 75% ee (95 : 5) = Br, = t-bu: 83% ee (94 : 6) 42% ee = Br, = e: 93% ee (96 : 4) 91% ee Scheme 12. C 2 -t-bu
8 -Co -Co -Co 2 CC 2 catalyst C 2 - C 2 17, = t-bu: 2% ee (7 : 93) 98% ee (hν) 18, = t-bu: -% ee (2 : 98) -98% ee (I) 18, = Et: -% ee (1 : 99) -99% ee (I) I= -methylimidazole : proposed approach of olefin u Cl Co 17 Scheme (5 mol %) 2 C 2 3 -methylimidazole 1 TF, r.t. 3 1 =, 2, 3 =: 97% ee, 67% =, 2 = e, 3 =: 90% ee, 70% 17 (5 mol%), hν 2 Co e e 3 C 2 TF (5 ml), r.t., 16 h =, 2, 3 =: 94% ee, 78% 1 = (C 3 ) 2 C=C(C 2 ) 2, 2 = e, 3 =: 90% ee, 70% Scheme 14.
9 L 1 L 1 β β L 2 µ Fig. 4 L 2 µ-oxo-trans µ-oxo-cis µ Fig. 4. L 1, L 2 β Fig. 2 β - β µ Belokon β µ µ µ µ β Scheme 15 Sie 3 20 C e 3 SiC C = : 86% ee, =4-eC 6 4 : 84% ee Cl Cl 2 Et 3 20 t-bu Bu-t t-bu Bu-t 20 C e 3 SiC C C Sie 3 C C e 3 SiC C Scheme 15. C C
10 µ β Scheme 16 µ Scheme 17 µ Scheme 16 di-µ-oxo (salen) e-d e-d 4 CD e-d 4 21 CD 3 trans-(salen) complex Scheme S e urea 2 2 S e 98%ee, 78% n-c 8 17 S e 23 n-c 8 17 S e urea % ee, 70% S S 23 (2 mol%), UP (1.0 eq) e, 0 C, 24h = S S 99% ee, 91% trans /cis >99 : 1 Cl Cl = Bn 99% ee, 93% 94 : 6 (,)-(salen) 22 2, Et 3 C 2 Cl 2, r.t. di-µ-oxo (salen) Scheme 17. Baeyer-Villiger Scheme 18 Criegee σ σ L s : L.. B: L s Criegee intermediate :B s > B: Scheme 18. L L.. s : s
11 L S S L Baeyer- Villiger Criegee = β Baeyer-Villiger β Scheme 19 catalyst, 2 2 C 2 Cl 2, r.t. 24: 20%, 0% ee 25: 30%, 57% ee 25: 72%, 77% ee (Et, -20 C) t-bu Co Bu-t F Co F SbF 6 SbF 6 Bu-t t-bu F F Scheme 19. Criegee β Baeyer-Villiger Scheme 20 Baeyer-Villiger normal abnormal Scheme (5 mol%), UP C 2 Cl 2, r.t. = C UP= urea : 87% ee, 68% 2 = p-ec 6 4 : 84% ee, 43% = n-c 8 17 : 81% ee, 63% 26 (5 mol%), UP C 2 Cl 2, r.t. 94% ee, 99% = Scheme 20. Zr 26
12 (matching pair) slow isomer (racemic) 26, UP, ClC 6 5 r.t. normal lactone 40 : 1 ent-abnormal lactone fast isomer (mis-matching pair) ent-normal lactone 1 : 35 abnormal lactone Scheme 21. Scheme 22 Scheme 23 ( 2) 27, air, hν, r.t. k S /k = 20 65% conversion >99.5% ee u Cl 65% ee 27 Scheme hν, 2 C u III Cl 2 hν 2 or 2 P u IV Cl 2 C= P= or non 2 C P u III Cl or 2 u III Cl Scheme 23.
13 Scheme 24 28, hν, air d 6 -benzene, r.t., 12 h quantitative 0% n 28, air, hν ether n n= 1: 81% n= 2: 95% t-bu Scheme 24. u Cl Bu-t t-bu 28 Bu-t Scheme 25 29, air, hν CCl 3, r.t. 80% ee, 80% e e u Ar Ar 29 Scheme 25. Ar= p-c 6 5 C 6 4 CEST
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