Absolute Asymmetric Synthesis [AAS] by Photochemistry on Solid-State
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![Absolute Asymmetric ynthesis [AA] by otochemistry](/docs-images/75/71724631/images/1-0.jpg "on olid-tate Qihui Jin upergroup eting ept.")
1 Absolute Asymmetric ynthesis [AA] by otochemistry on olid-tate Qihui Jin upergroup eting ept. 28, 2005
2 What is an absolute asymmetric synthesis? Absolute asymmetric synthesis: An asymmetric synthesis starting from an achiral reagent and in the absence of any external chiral agent Achiral Chiral spontaneous chiral crystallization photochemical reaction Chiral Crystal
3 Chiral Crystal A crystal lacking both a center of symmetry and a glide plane is defined as chiral. uch a chiral crystal must belong to a chiral space group. pace group: 230 Chiral pace Group: 65 Table: The 10 most common space groups: rder pace group % rder pace group % 1 P2 1 /c Pbca PĪ Pnma P Pna P Pbcn C2/c P1 1.1 achiral compound achiral crystal 8% chiral compound chiral crystal enantiomorph akamoto, M. In Molecular and uparamolecular otochemistry: vol 11, Chiral otochemistry; Inoue, Y.; Ramamurthy, V. Eds; Marcel Dekker: ew York; 2004, p
4 Asymmetric Induction by Chiral Quartz l- and d-quartz Flack,. D. C i-pr 2 Zn t-bu l-quartz 93-97% t-bu 84-97% ee C i-pr 2 Zn t-bu d-quartz 90-97% t-bu 80-97% ee oai, K.; sanai,.; Kadowaki, K.; Yonekubo,.; hibata, T.; ato, I. J. Am. Chem. oc. 1999, 121,
5 Forming Desired Chiral Crystal pontaneous Chiral Crystallization: Equal chance to form D or L Crystal 32 different crystallizations of acl 3 14 L 18 D P2 1 3 L D Kondepudi, D. K.; Kaufman, R. J.; ingh,. cience 1990, 250, 975.
6 The First Absolute Asymmetric ynthesis Using Crystals space group P Br 2, gas Br 2, liquid Br Br Br Br 6% ee 0% ee Penzien, K.; chmidt, G. M. J. Angew. Chem. Int. Ed. Engl. 1969, 8, 608
7 Absolute Asymmetric otochemistry on olid-tate Unimolecular Di-π-thane otorearrangement Electrocyclization [2+2], [4+4] ydrogen Abstraction Followed by Cyclization Migration and Radical Pair Intermolecular ingle Component Crystal Cocrystal Racemic-to-Chiral
8 Di-π-thane otorearrangement Pr i 2 C C 2 Pr i i Pr 2 C C 2 Pr i P >95% ee Pr i 2 C C 2 Pr i Pr i 2 C C 2 Pr i Evans,. V.; Garcia-Garibay, M.; mkaram,,; cheffer, J. R.; Trotter, J.; Wireko, F. J. Am. Chem. oc. 1986, 108, Di-π-methane photorearrangement Zimmerman,. E.; Armesto, D. Chem. Rew. 1996, 96,
9 Di-π-thane otorearrangement a C C C C C C P o C 16% conv. b a C C 1 : 1.3 b C C C C 44% ee 87% ee Roughton, A. L.; Muneer, M.; Demuth, M.; Klopp, I.; Kruger, C. J. Am. Chem. oc. 1993, 115, 2085.
10 oto Electrocyclization solution 1,5- shift Toda, F.; Tanaka, K. uperamol. Chem. 1994, 3, % convesion P % ee Wu, L.-C.; Cheer, C. J.; lovsson, G.; cheffer, J. R.; Trotter, J.; Wang,.-L.; Liao, F.-L. Tetrahedron Lett. 1997, 38, 3135.
11 [2+2] Cycloaddition -45 o C P % yield, 40% ee akamoto, M.; okari,.; Takahashi, M.; Fujita, T.; Watanabe,.; Iida, I.; ishio, T. J. Am. Chem. oc. 1993, 115, 818. akamoto, M.; Takahashi, M.; Mino, T.; Fujita, T. Tetrahedron 2001, 57, P o C 84% yield, 20% ee akamoto, M.; Takahashi, M.; Arai, T.; himizu, M.; Yamaguchi, K.; Mino, T.; Watanabe,.; Fujita, T. Chem. Commun. 1998, 2315.
12 [2+2] Cycloaddition 15 o C 100% syn 91% ee + 60:1 anti akamoto, M.; Takahashi, M.; Arai, T.; Fujita, T.; Watanabe,.; Iida, I.; ishio, T.; Aoyama,. J. rg. Chem. 1993, 58, o C * + syn + 15:1 anti 20% yield, 88% ee 40% yield, 0% ee akamoto, M.; Takahashi, M.; Fujita, T.; Watanabe,.; ishio, T.; Iida, I.; Aoyama,. J. rg. Chem. 1997, 62, 6298.
13 [4+4] Cycloaddition R R R Yield, % ee, % P quantitative 82 P2 1 quantitative >99 Kohmoto,.; no, Y.; Masu,.; Yamaguchi, K.; Kishikawa, K.; Yamamoto, M. rg. Lett. 2001, 3, 4153.
14 Abstraction and Cyclization 0 o C P2 1 81% yield, 81% ee akamoto, M.; Takahashi, M.; Kamiya, K.; Yamaguchi, K.; Fujita, T.; Watanabe,. J. Am. Chem. oc. 1996, 118, o C P Pr i Pr i conrotatory Zwitterion 44% yield, 55% ee akamoto, M.; Takahashi, M.; Arai, W.; ino, T.; Yamaguchi, K.; Watanabe,.; Fujita, T. Tetrahedron 2000, 56, 6795.
15 Abstraction and Cyclization a b o C a P b 6% yield, 86% ee Irngartinger,.; Fettel, P. W.; iemund, V. Eur. J. rg. Chem. 1998, 2079.
16 Abstraction and Cyclization Cl 8 o C 8% conv. >80% ee Ar Evans,. V.; Garcia-Garibay, M.; mkaram,,; cheffer, J. R.; Trotter, J.; Wireko, F. J. Am. Chem. oc. 1986, 108, 5648.
17 Migration of Radical Pair (o-tol) 0 o C (o-tol) (o-tol) P % yield, 30% ee akamoto M.; Takahashi, M.; Moriizumi,.; Yamaguchi, K.; Fujita, T.; Watanabe,. J. Am. Chem. oc. 1996, 118, R R R R P R = 0 o C, 100% yield, 83% ee R = 50 o C, 25% yield, 87% ee akamoto M.; eikine,.; Miyoshi,.; Mino, T.; Fujita, T. J. Am. Chem. oc. 2000, 122,
18 Intermolecular [2+2] Et Et 2 C Et Et 2 C Et Et 2 C C C 2 Et Et 2 C C C 2 C C 2 C C 2 100% ee + trimer + oligomers Addadi, L.; van Mil, J.; Lahav, M. J. Am. Chem. oc. 1982, 104, 3422.
19 Intermolecular [2+2] C 2 Et Et 2 C -40 o C C 2 Et P2 1 Et 2 C 45% yield, 95% ee asegawa, M.; Chung, C.-M.; Muro,.; Maekawa, Y. J. Am. Chem. oc. 1990, 112, 5676.
20 Intermolecular [2+2]: Cocrystal 15% Th Ar Ar Ar 29% conv. Th Ar Ar + Th Ar Ar Ar = 2,6-ClC 6 3 Th = 2-thienyl 70% ee Elgavi, A.; Green, B. G.; chmidt, G. M. J. J. Am. Chem. oc. 1973, 95, C C 91% C C * C C C C P2 1 95% ee uzuki, T.; Fukushima, T.; Yamashita, Y.; Miyashi, T. J. Am. Chem. oc. 1994, 116, 2793.
21 Cocrystal For AA RT 37% yield, 35% ee P Koshima,.; Ding, K.; Chisaka, Y.; Matsuura, T. J. Am. Chem. oc. 1996, 118,
22 Frozen Molecular Chirality morized by Chiral Crystallization Kcal/mol at K () (R) + A B T, C Conditions Yield, % A : B A, ee, % B, ee, % 15 olid tate :5 >99-0 TF - 67: TF - 68: TF - 81: akamoto, M.; Iwamoto, T.; ono,.; Ando, M.; Arai, W.; Mino, T.; Fujita, T. J. rg. Chem. 2003, 68, 942.
23 Chirality Retention: From olid-tate to omogenous olution P P [R,R] P P R[,] P P [R,R] PdCl 2 (C 3 C) 2 DCM, -78 o C 16h P P Pt Cl Cl [R,R]-(+)-Cat Ac + ac(c 2 ) 2 1% [R,R]-(+)-Cat TF, 25 o C 93% 2 C C 2 80% ee Tissot,.; Gouygou, M.; Dallemer, F.; Daran, J.-C.; Balavoin, G. G. A. Angew. Chem. Int. Ed. 2001, 40, 1076.
24 Racemic-to-Chiral: ptical Activity Generated by Crystallization C 2 2 C C 2 2 C L-(+)-tartaric acid D-(-)-tartaric acid Louis Pasteur, 1947 pontaneous olid-tate Resolution: half-life 15 min at 50 o C -(+) R-(-) Pincock, R. E.; Wilson, K. R. J. Am. Chem. oc. 1970, 93, 1291.
25 ptical Enrichment of a Racemic Chiral Crystal by X-ray Irradiation Co C C Co (R) () P D enantiomorph Volumn of reaction cavity: R 7.49 Χ Χ Required volume for the racemization: 11.5 Χ sano, Y. T.; Uchida, A.; hashi, Y. ature 1991, 352, 510.
i-pr 2 Zn CHO N Sato, I.; Sugie, R.; Matsueda, Y.; Furumura, Y.; Soai, K. Angew. Chem., Int. Ed. Engl. 2004, 43, 4490
Asymmetric Synthesis Utilizing Circularly Polarized Light Mediated by the otoequilibration of Chiral lefins in Conjuction with Asymmetric Autocatalysis l-cpl r-cpl (S) () Sato, I.; Sugie,.; Matsueda, Y.;
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