Asymmetric Autocatalysis Triggered by Carbon Isotope ( 13 C/ 12 C) Chirality
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1 Asymmetric Autocatalysis Triggered by Carbon Isotope ( 13 C/ 12 C) Chirality Hong Ren
2 Asymmetric Autocatalysis Triggered by Carbon Isotope ( 13 C/ 12 C) Chirality Hong Ren
3 Asymmetric Autocatalysis Triggered by Carbon Isotope ( 13 C/ 12 C) Chirality Hong Ren
4 The Homochirality Remains a Puzzle
5 The Homochirality Remains a Puzzle All the 20 natural amino acids are left-handed. A proposed theory to explain the origin of the homochirality: 1 st step Shattering the mirror: Absolute Asymmetric Synthesis 2 nd step Propagating the imbalance: Asymmetric Autocatalysis Blackmond, D. G. PAS, 2004, 101,
6 Asymmetric Autocatalysis and Its Implications for the Chemical Origin of Life 2 Zn OZn H with low enantiomeric enrichment with hign enantiomeric enrichment CHO + 2 Zn Soai, K.; Shibata, T.; Morioka, H.; Choji, K. ature, 1995, 378,
7 Asymmetric Autocatalysis Triggered by Carbon Isotope ( 13 C/ 12 C) Chirality Hong Ren
8 Generation of Chirality by Carbon Isotope Substitution 12 C C 12 carbon isotope substitution 12 C C 13 X Y Achiral compound X Y Isotopic enantiomers Problem: Experimentally inaccessible: very small difference between 13 C and 12 C Solution: Asymmetric Autocatalysis
9 Discrimination of the Carbon Isotopic Chirality by Asymmetric Autocatalysis H H 13 3 CO OCH 3 Carbon Isotopic Enantiomers H H 3 CO O 13 CH 3 (S)-2 (R)-2 H 3 C 13 CH C C H 13 C 13 C13 C C 13 H 3 13 C CH 3 H C C C C 13 C13 C (R)-1 (S)-3 (S)-1 (R)-3
10 Discrimination of the Carbon Isotopic Chirality by Asymmetric Autocatalysis 4 + Zn 2 CHO 4+ i-pr 2 Zn 4+ i-pr 2 Zn asymmetric autocatalysis OZn OZn asymmetric autocatalysis tiny ee tiny ee
11 Discrimination of the Carbon Isotopic Chirality by Asymmetric Autocatalysis Enhancement of Enantiomeric Excess (S) (R) Highly Enantioenriched (S)-5 Highly Enantioenriched (R)-5
12 Synthesis of Compound 1---Route 1 O Ti(Oi-Pr) 4, toluene 13 CH 3 + Me 2 Zn H 3 C 13 CH 3 (R)-1, 89% ee ligand (-)-8 O + ( CH 13 CH 3 ) 2 Zn 3 Ti(Oi-Pr) H 13 3 C 4, toluene CH 3 (S)-1, 93% ee SHO 2 H H SO 2
13 Synthesis of Compound 1---Route 2 HO CO 2 i-pr 13 CH 2 HO DIPT CO 2 i-pr Ti(Oi-Pr) 4, t-buo, DCM H 13 2 C O anhydride, DMAP, pyridine 1) p-toluenesulfonic 2) LAH, ether H 3 C 13 CH 3 (R)-1, 86% ee H 13 3 C CH 3 (S)-1, 90% ee
14 Synthesis of Compound 2 O H a, OCH 13 CH 3 H 13 3 CO OCH 3 3 (S)-2 1) 3 P, diisopropyl azodicarboxylate, p-o 2 C 6 H 4 CO, THF 2) K 2 CO 3, Me H H 3 CO O 13 CH 3 a, 13 CH 3 O OCH 3 (R)-2
15 Synthesis of Compound 3 13 C 6 H 5 CHO CH 3 Br H C C C C C13 13 C (R)-3, 99% ee 1) TMSCl, TEA, THF 2) n-buli, B(OEt) 3, THF 3) diethylzinc, toluene then H 2 O 4) TBAF, THF (p-br)c 6 H 4 B() 2 diethylzinc, toluene C C H C C 13 C13 C Br (S)-3, 96% ee H C C C C 13 C13 C C C H 13 C 13 C13 C C 13 (R)-3, 99% ee (S)-3, 96% ee
16 Chiral Discrimination of the Isotopic Carbons Using Compound 1 from Route 1 Entry Chiral alcohol Isolated yield ee configurition 1 (R)-1 (89% ee) S 2 (S)-1 (93% ee) R 3 (R)-1 (89% ee) S 4 (S)-1 (93% ee) R 5 (R)-1 (89% ee) S 6 (S)-1 (93% ee) R 7 (R)-1 (89% ee) D 93 S 8 (S)-1 (93% ee) R
17 Chiral Discrimination of the Isotopic Carbons Using Compound 1 from Route 2 Entry Chiral alcohol Isolated yield ee configurition 1 (R)-1 (86% ee) S 2 (S)-1 (86% ee) R 3 (R)-1 (86% ee) S 4 (S)-1 (90% ee) R 5 (R)-1 (86% ee) S 6 (S)-1 (84% ee) R 7 (R)-1 (86% ee) S 8 (S)-1 (90% ee) R
18
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