Enantioselective Benzoin Reactions
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1 Enantioselective Benzoin Reactions GUAQU ZAG DEMARK GRUP PREETATI
2 Benzoin benzoin benzoic acid Industrially used in powder coating to prevent pinholes In organic chemistry used to prepare benzil, a photoinitiator benzoin is a 1,2-hydroxy ketone benzil 1,2-hydroxy ketone benzoin reaction 1,3-hydroxy ketone aldol reaction 1,4-hydroxy ketone tetter reaction 2
3 Discovering Benzoin Reaction C amygdalin prunasin C bitter almond 2 enzyme kernel sweet almond avg. C content 25 mg/kg C bitter almond 1062 mg/kg apricot kernel 851 mg/kg each bitter almond contains 4-9 mg C acute oral lethal dose of C = mg/kg West J d. 1982, 136, IR Toxicology 2013.
4 Discovering Benzoin Reaction 1832: Wöhler and Liebig C -C C 1903: Lapworth KC, 2 K C C 2 Roles of cyanide: (1) good nucleophilile (2) anion stabilizing group (3) good leaving group C Wöhler, F.; Liebig, J. Ann. arm. 1832, 31, 249. Zinin, Ann. arm. 1835, 34, Lapworth, A. J. Chem. oc. 1903, 83, 995.
5 Thiazolium-Catalyzed Benzoin 1943: Ugai Br a (1 equiv), not observed observed Br Et Br Bn Br Bn I I Br Bn 1958: Breslow worked didn t work R base R zwitterion R PT R R Breslow intermediate Ugai, T.; Tanaka,.; Dokawa,. J. arm. oc. Jpn. 1943, 63, Breslow, R. J. Am. Chem. oc. 1958, 80, 3719.
6 Thiamine - ature s C Catalyst C 3 2 thiamine C 3 x-ray structure of thiamine-dependent transketolase enzyme schematic view J. Biol. Chem. 1993, 268, J. Biol. Chem. 1997, 272, 1864.
7 Asymmetric Benzoin Reaction Asymmetric omo-benzoin Different C catalyst designs Asymmetric Intramolecular Crossed Benzoin Asymmetric Intermolecular Crossed Benzoin Varying carbonyl acceptors (C) Varying carbonyl donors (MP, LB) 7
8 Asymmetric Thiazolium Catalysts 1966: heehan Br 0.1 equiv * Et 3 (0.1 equiv), the precipatate 50% yield, 0.77% optical purity the rest of crude after chromatography 9% yield, 22% optical purity 1974: heehan Br best enantioselectivity 6.1% yield 51.5% optical purity 3 Br best yield 78% yield 7.8% optical purity 1974: Tagaki 1993: López-Calahorra ipr best enantioselectivity 20% yield 35.3% optical purity I I best yield 21% yield 63:37 er heehan, J.; unneman, D.. J. Am. Chem. oc. 1966, 88, heehan, J.; ara, T. J. rg. Chem. 1974, 39, Tagaki, W.; Tamura, Y.; Yano, Y. Bull. Chem. oc. Jpn. 1980, 53, Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521.
9 Asymmetric Triazolium Catalysts 1996: Enders Ar cat mol% K 2 C 3, TF Ar Ar 4 Ar yield % er : C : 7 4-C : 9 4-FC : 28 4-C : BrC : 40 deprotonation here lead to decomp. 1999: Enders first comm. avail. carbene no data on cat. activity Enders, D.; Breuer, K.; Teles, J.. elv. Chim. Acta 1996, 79, Teles, J..; Breuer, K.; Enders, D.; Gielen,. ynth. Commun. 1999, 29, 1.
10 Bicyclic Thiazolium and Triazolium Catalysts : Leeper Tf TB 34% yield 60:40 er 2002: Enders = tate of the Art Ms 20% yield 55:45 er Tf TB 50% yield 60:40 er 45% yield 90:10 er Ar cat. 0.1 equiv Kt-Bu, TF Ar Ar BF 4 80~90% yield > 90 : 10 er Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, Gerhards, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, Knight, R. L.; Leeper, F. J. J. Chem. oc., Perkin Trans , Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743.
11 Transition tate Calculations disfavored 11 Dudding, T.; ouk, K.. Proc. atl. Acad. ci. 2004, 101, 5770.
12 otable ntions of Chiral Catalysts 4 4 tbu tbu Bn Bn 2 Br new design bad selectivity Ar = 3,5-dimethylphenyl Pesch, J.; arms, K.; Bach, T. Eur. J. rg. Chem. 2004, Benagla, M. et al. Tetrahedron: Asymmetry 2003, 14, Tachibana, Y.; Kihara,.; Takaka, T. J. Am. Chem. oc. 2004, 126, 3438.
13 ynthesis of C Catalysts Thiazollium salts: Triazollium salts: 2 K, 2 Bicyclic Thiazollium salts: P 3 DCM C 2 R 3 Ac 2 R 3 40~60% (1),, 2 TB Tf 2, pyr, DCM Kt-Bu, TF (2) TB, Et 3, DMAP, DCM Tf TB heehan, J.; ara, T. J. rg. Chem. 1974, 39, Teles, J..; Breuer, K.; Enders, D.; Gielen,. ynth. Commun. 1999, 29, Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611.
14 ynthesis of C Catalysts Bicyclic Thiazollium salts: P3, LiI, ; then (1) Ts 2, aac, DME (2),, 2 (2) TB, Et 3, DMAP, DCM TB Tf 2, pyr, DCM Tf TB Bicyclic Triazollium salts: R 3 BF 4 R 3 R C() 3 R Enders Triazollium salt: t-bu 3 BF 4 t-bu 3 t-bu C() 3 t-bu Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, Teles, J..; Breuer, K.; Enders, D.; Gielen,. ynth. Commun. 1999, 29, Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743.
15 Crossed Benzoin Reactions Aryl Alkyl cat. 0.1 equiv Et 3, Et Aryl Bn Alkyl Aryl Alkyl A B cat. Aryl alkyl AB yield % A : B ratio ipr : 75 2-C 6 4 ipr : 0 2-C : C 6 4 ipr : 55 2-furyl ipr : 5 2-furyl npr : 15 n-hept ipr : 70 trend? R R =, Et, npr, ipr, Cy,, 2-furyl cat. 0.1 equiv Et 3, Et R 74~100% yield 64~100% selectivity cat. tetter,.; Dämbkes, G. ynthesis 1977, 403. tetter,.; Dämbkes, G. ynthesis 1980, Matsumoto, T.; hishi, M.; Inoue,. J. rg. Chem. 1985, 50, 603. Et Br
16 Intramolecular Crossed Benzoin cat. 0.2 equiv Et 3, DMF, 96 h cat. 0.2 equiv 69% cat. Bn C Et 3, DMF, 24 h 47% cat. 0.2 equiv Et 3, DMF, 24 h % 11% cat. 0.2 equiv Et 3, DMF, 24 h 4 4 0% 40% They were really encouraged by these results... Enders, D.; iemeier,. ynlett 2004, achisu, Y.; Bode, J. W.; uzuki, K. Adv. ynth. Catal. 2004, 346, 1097.
17 Asymmetric Intramolecular Crossed Benzoin R cat. 0.2 equiv Et 3, DMF, 96 h R 80~90% yield >97:3 er BF 4 R =, Et, nbu, ibu, Bn cat. the fused rings on the catalyst forces E geometry of the Breslow intermediate Enders et al Angew. Chem., Int. Ed. 2006, 45, Ronnis et al J. rg. Chem. 1996, 61, 5813.
18 Asymmetric Intramolecular Crossed Benzoin ynthesis of the tetracyclic triazoliumsalt Group Problem Br Et 2 6 steps (1) 3 BF 4 (2) 3 BF 4 (3) C() 3 Enders et al Angew. Chem., Int. Ed. 2006, 45, Ronnis et al J. rg. Chem. 1996, 61, 5813.
19 Asymmetric Intramolecular Crossed Benzoin ynthesis of the tetracyclic triazoliumsalt LDA, BrC 2 C 2 Et Et Li, 2, TF 2 4A M Et 3 i, Ti 4 Li, 2, DM, TF, 2 (1) 3 BF 4 (2) 3 BF 4 (3) C() 3 very selective catalyst difficult to access Enders et al Angew. Chem., Int. Ed. 2006, 45, Ronnis et al J. rg. Chem. 1996, 61, 5813.
20 First Asymmetric Crossed Benzoin R BFD 281A or BAL ThDP, Mg 2, KPi buffer DM, 30 o C R Br R yield % selectivity % er 3-C >99 >99 95 : 5 4-Br : CF 3 75 > : 3.5 3,4-C > 99 : 1 3,4,5-() > 99 : 1 3,5-() 2 >99 95 > 99 : 1 racemic BAL 25 equiv. acetaldehyde ThDP, Mg 2, KPi buffer DM, 30 o C Br single enantiomer thermodynamically controlled reaction? Br Müller et al. J. Am. Chem. oc. 2002, 124, Müller et al. Chem. Eur. J. 2000, 6, 1483.
21 First Asymmetric Crossed Benzoin 21 Müller et al. FEB J. 2005, 272, 6067
22 C-Catalyzed Asymmetric Crossed Benzoin Imine accepters: Ts cat equiv PEMP, DCM, 23 o C Trifluoromethyl ketone accepters: 15~100% yield 70~80% ee I cat. Bn Boc Aryl F 3 C Aryl' cat. 0.1 equiv ipr 2 Et, TF, 0 o C Aryl Aryl' CF 3 α-ketoester accepters: 71~86% yield 60~80% ee TBDP cat., = alkyl, aryl C 2 Et cat. 0.1 equiv ipr 2 Et, C 2 2, 23 o C R2 C 2 Et 47~92% yield 77~94% ee ipr cat. BF 4 Miller et al. J. Am. Chem. oc. 2005, 127, Enders et al. Chem. Commun. 2010, 46, Gravel et al. rg. Lett. 2013, 15,2214.
23 C-Catalyzed Asymmetric Crossed Benzoin α-ketoester accepters with DKR: Aryl X = or Br R = alkyl, aryl Et 2 C X racemic R cat equiv K 2 C 3, TBME, rt Aryl X C 2 Et 40~95% yield > 10 : 1 dr > 94 : 6 er R cat. s BF 4 Alkynone acceptors:, R 3 = alkyl, aryl = CF 3 or R 3 cat. 0.2 equiv K 2 C 3, /, -15 o C R2 51~99% yield > 95 : 5 er R 3 cat. s BF 4 Using an electron-deficient ketone accepter The state of the art catalyst = Enders tetracyclic triazoliumsalt Goodman, C. G.; Johnson, J.. J. Am. Chem. oc. 2014, 136, Vicario et al. Chem. Eur. J. 2015, 21, 8384.
24 Kinetic Control Model reaction Ts t-bu Racemization experiment cat. (0.1 equiv) Et 3 (15 equiv) DCM, 35 o C, 24 h 75% t-bu cat. Bn Cross-over experiment Ts I (0.1 equiv) Cy D Et 3 (15 equiv) DCM, 35 o C D Cy > 95% D atom C Ts Bn 0.5 equiv t-bu Cy I (0.1 equiv) Et 3 (15 equiv) DCM, 35 o C no cross-over Cy C Bn t-bu Product formed under kinetic control 24 Murry et al. J. Am. Chem. oc. 2001, 123, 9696.
25 Thermodynamic Control? 1.2 equiv 1 equiv 0.6 equiv 1 equiv cat. (0.2 equiv) Et 3 (0.2 equiv) Et, 70 o C, 2-3 d cat. (0.2 equiv) Et 3 (0.2 equiv) Et, 70 o C, 2-3 d 82% 71% cat. Bn Cross-over experiment: cat. (0.2 equiv) Et 3 (0.2 equiv) Et, 70 o C, 2-3 d 1 equiv 1 equiv 3.7% cross-over observed! Benzoin formation is reversible under these conditions 25 You et al. Chem. Commun. 2007, 852
26 Partial Thermodynamic Control? F 3 C 1 equiv 1.3 equiv cat. (0.1 equiv) i-pr 2 Et (1 equiv) TF, 0 o C, 24 h CF 3 TBDP cat. BF 4 homo-benzoin formation is reversible crossed benzoin product is kinetically trapped 26 Enders et al. Chem. Commun. 2010, 46, 6282.
27 Kinetic Control? Model reaction cat equiv Br K 2 C 3 (1 equiv) Et 2 C Br TBME, rt C 2 Et 2 equiv racemic 91% 9% Cross-over experiment s BF 4 cat equiv Br Et 2 C K 2 C 3 (1 equiv) Br TBME, rt C 2 Et not observed cat. benzoin formation is irreversible under these conditions 27 Johnson et al. J. Am. Chem. oc. 2014, 136,
28 Asymmetric ilyl Benzoin Cyanide-catalyzed benzoin reaction: KC KC -KC K C C K C K Chiral C catalyst = equivalent of chiral cyanide But still, too many steps are potentially reversible More ways to control the reaction selectivity: (1) Controlling the exchanging protons (2) a different chiral cyanide that s not C? (3) maybe a chiral metal cation can exist 28
29 Asymmetric ilyl Benzoin Chiral Cyanide iet 3, = aryl cat. (0.075 equiv) n-buli (0.2 equiv) TF, 0-25 o C, 30 min iet 3 60~90% yield up to 95 : 5 er Ar Ar Ar P Ar Ar = 2-F ilyl ketone is used in place of aldehyde as the carbonyl donor silyl group transfer is more restricted than proton transfer TADDL - metallophosphite = chiral cyanide iet 3 M"C" iet 3 M"C" 1,4-silyl migr. M 1,2-Brook Rearr. "C" iet 3 iet 3 M "C" enantio-determining iet 3 "C" M 29 Johnson et al. J. Am. Chem. oc. 2004, 126, 3070.
30 Asymmetric ilyl Benzoin Chiral tal R iet 3 cat equiv C iet 3 toluene, 45 o C C Bn C 2 Bn 70~90% yield up to 90 : 10 er Johnson et al. J. rg. Chem. 2004, 69, Johnson et al. Angew. Chem. Int. Ed. 2004, 43, 2652.
31 Asymmetric ilyl Benzoin Chiral tal R iet 3 cat equiv C iet 3 toluene, 45 o C C Bn C 2 Bn Catalytic cycle with (salen)al-c 70~90% yield up to 90 : 10 er Al ipr tbu tbu iet 3 "M"C Et 3 i C C 2 M = (salen)al "M"C "M" C iet 3 1,2-Brook Rearr. iet 3 C C "M" enantio-determining iet 3 C "M" C Johnson et al. J. rg. Chem. 2004, 69, Johnson et al. Angew. Chem. Int. Ed. 2004, 43, 2652.
32 Asymmetric Benzoin with Lewis Base Lewis Base catalyzed benzoin reaction R 3 i C Pg cat* Pg -Pg -C -silyl oxyketene imine: modified carbonyl donor Chiral Lewis Acid-Base complex activates the carbonyl acceptor R 3 i Pg R 3 i i 3 (LB) 2 C Pg Pg LB LB i LB LB i 4 LB LB i P cat* 2 C 2 Denmark,. E.; Wilson, T. ature Chem. 2010, 2,
33 Asymmetric Benzoin with Lewis Base i-pr 3 i C t-bu i 4 (1.1 equiv) i-pr 2 Et (1 equiv) cat* (2.5 mol%) DCM, -78 o C, 2 h t-bu > 84% yield > 96 : 4 dr > 99 : 1 er (3.3 equiv) KF/aC 3 (aq.) 78~84% yield > 99 : 1 er P 2 C 2 Extremely selective reaction! n the other hand, substrates need to be specially prepared: C isobutylene (25 equiv) Ms (0.4 equiv) C t-bu KMD (1.2 equiv) i-pr 3 i (1.1 equiv) i-pr 3 i C t-bu R DCM, 24 o C, 60 h R TF, -78 o C, 2 h R =,, Et, i-bu, Bn 50~70% yield 93~97 yield Denmark,. E.; Wilson, T. ature Chem. 2010, 2,
34 ummary Asymmetric omo-benzoin Bicyclic triazolium salt BF 4 BF 4 Asymmetric Intramolecular Crossed Benzoin Tetracyclic triazolium salt Asymmetric Intermolecular Crossed Benzoin Tetracyclic triazolium salt Lewis Acid-Base catalyst P 2 C 2 34
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