Literature Report IX. Cho, S. H. et al. Org. Lett. 2016, 18, Cho, S. H. et al. Angew. Chem. Int. Ed. 2017, 56,
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1 Literature Report IX ynthesis of β-aminoboronates by Copper(I)- Catalyzed Addition of Diborylalkanes to Imines Reporter Checker Date : hubo Hu : Xiaoyong Zhai : Cho,. H. et al. rg. Lett. 2016, 18, Cho,. H. et al. Angew. Chem. Int. Ed. 2017, 56,
2 Contents 1 Introduction 2 Addition of Diborylmethane to Aldimines 3 Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines 4 ummary
3 CV of eung Hwan Cho Education: B.. in Chemistry KAIT Researcher at KAIT Ph.D. in Chemistry KAIT (Prof. ukbok Chang) Postdoc. at KAIT (Prof. ukbok Chang) Postdoc. at UC Berkeley (Prof. John F. Hartwig) eung Hwan Cho Assistant Professor Dept. of Chemistry, PTECH Research: Transition-metal-free C-C/C-B bond formation reactions; Transition-metal-catalyzed chemo-, regio-, and stereoselective C-C bond formation reactions. 3
4 Introduction 4
5 Introduction Fernández, E. et al. Chem. Commun. 2012, 48,
6 Introduction Hirano, K.; Miura, M. et al. J. Am. Chem. oc. 2013, 135,
7 Introduction Lin, G.-Q. et al. rg. Lett. 2014, 16, Takeda, Y. ; Minakata,. et al. Chem. ci. 2016, 7,
8 Introduction Ar N t Bu H + pinb Bpin [Cu] achiral phosphine Li t Bu, 50 o C Ar HN t Bu Bpin up to 98% dr Cho,. H. et al. rg. Lett. 2016, 18, Cho,. H. et al. Angew. Chem. Int. Ed. 2017, 56,
9 Addition of Diborylmethane to Aldimines Entry a Base (3 eq.) [M] (10 mol%) L (10 mol%) Conv. (1a) (%) Yield (4a) (%) dr (4a) 1 Li t Bu <1 <1 n.d. 2 Na t Bu /23 3 K t Bu /46 4 Li t Bu [Rh(CD)Cl] 2 dppben /17 5 Li t Bu Cu(Tf) 2 dppben /3 6 Li t Bu Cu(Tf) 2 dppb /5 7 Li t Bu Cu(Tf) 2 PPh /4 8 Li t Bu Cu(Tf) 2 PCy /5 9 Li t Bu CuCl dppben /2 10 Li t Bu CuBr dppben / CuBr dppben <1 <1 n.d. 12 Li t Bu CuBr n.d. 9
10 Addition of Diborylmethane to Aldimines HN t Bu H 4a, 85%, 99/1 dr t Bu HN t Bu H 4b, 76%, 90/10 dr t Bu F 3 C 3 HN t Bu H 4c, 87%, 99/1 dr t Bu HN H 4d, 75%, 98/2 dr HN H 4e, 82%, 97/3 dr F Cl Br HN H 4f, 70%, 98/2 dr HN t Bu H 4g, 61%, 97/3 dr Cl HN t Bu H 4h, 69%, 97/3 dr HN t Bu H 4i, 53%, 96/4 dr 10
11 Addition of Diborylmethane to Aldimines 11
12 Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines Entry a [Cu] olvent Yield (4a) (%) dr (4a) Ee (%) 1 CuBr dioxane 94 14/ CuBr THF 93 11/ CuBr Toluene <1 n.d. n.d. 4 CuBr dioxane/toluene (1:1) 98 (98) >20/ CuCl dioxane/toluene (1:1) 95 >20/ CuI dioxane/toluene (1:1) 71 >20/ Cu(NC) 4 PF 6 dioxane/toluene (1:1) 94 >20/ Cu(Ac) 2 dioxane/toluene (1:1) 94 >20/
13 Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines Entry a L Base Yield (4a) (%) dr Ee (%) 1 L1 Li t Bu 98 >20/ L2 Li t Bu 87 >20/ L3 Li t Bu 95 >20/ L4 Li t Bu 94 >20/ L5 Li t Bu <1 n.d. n.d. 6 L6 Li t Bu <1 n.d. n.d. Ar Ar Ar Ar P P R L1, R = N 2 ; L2, R = NEt 2 ; L3, R = N(CH 2 CH 2 ) 2 ; L4, R = NBn; N Ar = 4-C 6 H 4 7 L1 Na t Bu 13 2/1 n.d. 8 L1 K t Bu 54 1/1 n.d. P Ph N 9 L1 Li t Am 81 19/1 98 Ph 13
14 Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines NH NH NH NH H 4a, 98% >20/1 dr, 99% ee H H 4b, 97% 4c, 93% 18/1 dr, 98% ee 15/1 dr, 98% ee F H 4d, 89% 15/1 dr, 98% ee NH NH NH NH Cl H 4e, 83% 11/1 dr, 99% ee Br H 4f, 87% 10/1 dr, 97% ee H 4g, 97% >20/1 dr, 96% ee H 4h, 86% 15/1 dr, 98% ee 14
15 Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines NH NH NH C 2 H 4 Ph C 2 H 4 C 2 H 4 TB H 4i, 77% >20/1 dr, 99% ee H 4j, 69% >20/1 dr, 99% ee H 4k, 81% >20/1 dr, 93% ee NH NH NH 2 H 4l, 42% >20/1 dr, 93% ee H 4m, 83% >20/1 dr, 98% ee H 4n, 67% >20/1 dr, 99% ee 15
16 Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines Entry a R 1 R 2 Yield (%) dr Ee (%) 1 H 92 (6a) 3.2/1 94 (67) 2 H Pr 67 (6b) 3.5/1 98 (91) 3 H C 2 H 4 Ph 53 (6c) 4.9/1 98 (94) (6d) 3.6/1 96 (76) 5 4-Cl 65 (6e) 3.2/1 96 (77) 16
17 Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines Ph NH 2 CH Boc 2 dioxane, H 2 1M NaH, 1 h Ph NHBoc CH N H 2 Cl DCC, NEt 3, CHCl 3, 1 h Ph NHBoc N CH 3 MgBr THF, rt Ph NHTs H (1,2R)-6a 1) TFA, CH 2 Cl 2 2) Et 3 N, TsCl Ph NHBoc H NaBH 4 H, -20 o C, 1 h Ph NHBoc 17
18 Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines NH Bpin 3a, 99% ee 1) H 2 2, NaHC 3 THF/H 2, rt, 3 h 2) LAH, THF, 60 o C then Boc 2 at rt H NHBoc H 7, 68% >20/1 dr, 98% ee DEAD, PPh 3 CH 2 Cl 2, 0 o C to rt () 8, 89% >20/1 dr, 98% ee NHBoc 18
19 Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines NH R Bpin 3 H 2 D N Li R Bpin CuBr/L* Li t Bu LiBr Cu(L*) t Bu Bpin A 2 R Bpin Li t Bu N Cu(L*) R (L*)Cu R C Bpin B Bpin N 1 H 19
20 ummary Cho,. H. et al. rg. Lett. 2016, 18, 1210; Angew. Chem. Int. Ed. 2017, 56,
21 The first paragraph Chiral organoborons are an important class of synthetic intermediates which can undergo a range of carbon carbon and carbon heteroatom bond-forming reactions by stereospecific couplings. The synthesis of such compounds containing a nitrogen functionality at the β-position of the chiral boron unit is of significant importance in synthetic chemistry because they serve as versatile building blocks in many biologically active compounds. Consequently, several synthetic methods have been developed to afford chiral β-aminoborons. In this context, several elegant catalytic enatioselective methods have emerged for the preparation of chiral β-aminoborons under mild reaction conditions. Despite these advances, the development of a new approach from readily accessible imines remains elusive but is highly desirable. 21
22 The last paragraph In summary, we have developed a highly diastereo- and enantioselective, copper-catalyzed 1,2-addition of 1,1-bis[(pinacolato)boryl]alkanes to N- protected imines. With a CuBr/chiral phosphoramidite catalyst and Li t Bu, the reactions proceed to generate a broad range of b-aminoboronate esters with contiguous stereocenters in high yields. The products are highly synthetically useful, as demonstrated by further functionalizations of the Bpin unit to form new C- or C-C bonds upon C-B bond cleavage. Efforts to expand the scope of the diastereo- and enantiostereoselective 1,2-addition employing 1,1-bis[(pinacolato)boryl]alkanes are currently underway in our laboratory. 22
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