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Catalyzed Enantioselective Anti-Carboboration of Alkenyl Carbonyl Compounds

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Catalyzed Enantioselective Anti-Carboboration of Alkenyl Carbonyl Compounds COMMUNICATION Directed, Palladium(II)-Catalyzed Enantioselective anti-Carboboration of Alkenyl Carbonyl Compounds Zhen Liu, Xiaohan Li, Tian Zeng, Keary M. Engle* Abstract: A substrate-directed enantioselective and electron-deficient olefins (L11–L13) also failed to exert anti-carboboration reaction of alkenes has been developed, any chiral induction. To our delight, screening of monodentate wherein a carbon-based nucleophile and a boron moiety are imidazoline (MIM)(L15–L17) and MOX ligands (L18–L39) installed across the C=C bond through a 5- or 6-membered gave us reasonable levels of enantioselectivity, showing that palladacycle intermediate. The reaction is promoted by a these ligand scaffolds are privileged in this reaction. We palladium(II) catalyst and a mondentate oxzazoline ligand. A decided to choose the MOX scaffold for further optimization range of enantioenriched secondary alkylboronate products were based on synthetic accessibility considerations. The effect of obtained with moderate to high enantioselectivity that could be different MOX ligands on the alkene carboboration reaction is further upgraded by recrystallization. This work represents a new similar to the trends in He, Peng, and Chen’s report.[2c] method to synthesize versatile and valuable alkylboronate building blocks. Building on an earlier mechanistic proposal by Tryptophan-derived ligands showed higher levels of chiral Peng, He, and Chen, a revised model is proposed to account for induction than other amino acid derivatives in terms of chiral the stereoconvergent nature of this transformation. induction. Systematically varying the N-aryl group revealed that the steric and electronic nature of the substituents Substrate-directed nucleopalladation offers a powerful impacts both yield and er (albeit to a minor extent), with platform for generating multiple consecutive stereocenters electron-withdrawing groups proved to be advantageous. (Scheme 1A). The key feature of these transformations is the Ultimately, our optimization efforts converged with earlier [2c] formation of a stabilized 5- or 6-membered metallacycle findings from the aforementioned study in identifying L34, intermediate, which enables trapping with an additional which bears a 3,5-bis-CF3-phenyl substituent on the indole reaction partner, such as a proton, an electrophile, or a nitrogen, as the optimal ligand, providing up to 94:6 er and nucleophile, under various redox manifolds. Recently, our 71% yield. Interestingly, 3,5-bis-nitro-phenyl substituted group[1] and others[2] have developed numerous alkene ligand L36 also offered the same enantioselectivity, albeit hydrofunctionalization and 1,2-difunctionalization reactions by with slightly lower yield. Additionally, several oxazolines exploiting this approach. A frontier in this area of research is bearing a phenyl or methyl group at C-5 (L37–L39) were controlling the absolute stereochemistry of the products by prepared based on the idea that increased steric hindrance developing enantioselective variants of these could further improve the enantioselectivity. Unfortunately, transformations. In 2016, we reported a non-stereoselective none of these ligands performed better than L34. γ-selective hydrocarbofunctionalization, which was subsequently rendered enantioselective in 2018 by He, Peng, A. Versatile substrate-directed PdII-catalyzed alkene difunctionalization and Chen through the elegant design and development of a [2c] O X O monodentate oxazoline (MOX) ligand. In a complementary II cat. Pd Y N AQ line of inquiry using prochiral carbon nucleophiles, our H [X], [Y] R1 N R1 laboratory[1f] and the group of Zhang and Gong[2e] have (AQ) achieved enantioselective transformations with a chiral B. Overview of enantioselective variants: precedents and this work phosphoric acid (CPA) ligand and a chiral amine catalyst H O O II [C] ∗ cat. PdII cat. Pd H O respectively. Although these strategies have been successful AQ ∗ 1 ∗ AQ in enantioselective hydrocarbofunctionalization, R MOX Amine n [He, Peng, O R3 n = 1–3 enantioselective alkene 1,2-difunctionalization within this Chen, 2018] [Zhang, Gong, 2019] AQ family of reactions has not been reported to date. Herein, we 1 MeO O H O R Bpin O II cat. PdII ∗ cat. Pd [C] ∗ describe the first asymmetric alkene anti-carboboration R2 ∗ AQ [3] AQ n reaction via directed nucleopalladation. As in our previously NHCOAr1 CPA MOX R1 n = 1, 2 [4] [Engle, 2019] reported racemic version, the reaction proceeds smoothly this work via either 5- or 6-membered palladacycle intermediates. Ar3 Ar2 Furthermore, the resulting enantioenriched organoboron O [5] N Ph Me O O compounds are highly valuable in organic synthesis. P N N Ph O OH To begin our study, we selected N-methylindole (2a) as H OH Ar3 the nucleophile, B2pin2 (3a) as boron coupling partner, and 2 3 [6] Ar = 3,5-(CF3)2C6H3 Ar = 2,4,6-(Cy)3C6H2 8-aminoquinoline (AQ)-masked (Z)-3-hexenoic acid (1d) as MOX Ligand CPA Ligand Chiral Amine our pilot alkene substrate. In order to render this reaction Scheme 1. Background and Project Synopsis enantioselective, we carried out extensive screening of base, solvent, and reaction temperature, while at the same time examining a variety of chiral ligands (Table 1). Commonly used bi- and tridentate oxazoline-based ligands as well as Yu’s APAO[7] and MPAAM[8] ligands (L2–L10) only induced low to moderate enantioselectivity with attenuated reactivity. Initial screening of monodentate ligands such as CPA (L1) Z. Liu, X. Li, T. Zeng, Prof. K. M. Engle, Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, BCC-169, La Jolla, CA 92037 USA. E-mail: [email protected] Supporting information for this article is given via a link at the end of the document. Table 1. Screening of Chiral Ligands[a] Pd(OAc) (10 mol%) O Me 2 MeN Bpin O N L* (20 mol%), NaF (2 equiv) + + B pin ∗ AQ 2 2 AQ BQ (20 mol%), O2 (1 atm) ∗ Et HFIP/THF/DMF (2:2:1), 45 ºC Et 1d (0.05 mmol) 2a (3 equiv) 3a (4 equiv) 4f Ar Me Me Me Me O O O O O Me O N O O O O Me O P Ph Ph N OH N N N N N AcHN N Me O N N Bn Bn AcHN N Bn Me Ph Ph Ph Ph Me Ar Me Ar = 3,5-(CF3)2C6H3 L1, 50% L2, 7% L3, trace L4, 22% L5, 19% L6, 20% L7, 29% 52:48 er 32:68 er 55:45 er 31:69 er 53:47 er 53:47 er Me Me Bn Me Me OMe O Me Ph Ph Ph O O O2 O Me N O N N S S O N N O Me NMe2 N N O O2 AcHN AcHN AcHN O O O O Bn Me Me Me Me Me Me L8, 14% L9, 21% L10, 13% L11, 18% L12, 31% L13, 20% L14, 24% 50:50 er 50:50 er 50:50 er 50:50 er 50:50 er 50:50 er 51:49 er O Me Me H Ph Me Ph Ac Ph O O O N N N Me Me Me Me Me Me N N N N N N N Ph Ph Ph Me Ph Bn L15, 22% L16, 16% L17, 21% L18, 37% L19, 42% L20, 35% L21, 41% 79:21 er 73:27 er 80:20 er 80:20 er 42:58 er 28:72 er 86:14 er Ts Boc Me O O O O O O NH NH NH N N N Ph Me Et Me Me Me N N N N N N L22, 34% L23, 47% L24, 39% L25, 63% L26, 61% L27, 59% 86:14 er 88:12 er 86:14 er 90:10 er 92:8 er 92:8 er t-Bu Me MeO OMe Me Bn Me O t-Bu Me OMe O N N Me O Me N O O O N Me N N N N N Me Me Me N N N L28, 62% L29, 37% L30, 58% L31, 57% L32, 62% L33, 57% 89:11 er 91:9 er 92:8 er 90:10 er 92:8 er 93:7 er F3C F CF3 O2N F3C F3C F3C CF3 F F NO2 CF3 CF3 CF3 O O O O Ph O Me O Ph N N F N N N N Me Me Me Me Me Me N N N N N N L34, 71% L35, 70% L36, 63% L37, 62% L38, 62% L39, 61% 94:6 er 91:9 er 94:6 er 92:8 er 91:9 er 94:6 er [a] Reaction conditions: 1d (0.05 mmol), 2a (3 equiv), 3a (4 equiv), Pd(OAc)2 (10 mol%), chiral ligand (20 mol%), BQ (20 mol%), NaF (2 equiv), HFIP/THF/DMF 1 (2:2:1, 0.1 mL), 45 °C, O2 (1 atm), 5 d. Percentages refer to H NMR yields with CH2Br2 as internal standard. The enantioselectivity was determined by SFC analysis. After identifying the optimal ligand and reaction substrates (1b and 1c) resulted in the same major conditions, we next investigated the scope of this diastereomer after carboboration (4d and 4e), which is palladium(II)-catalyzed asymmetric alkene inconsistent with the stereoinduction and -convergence model anti-1,2-carboboration reaction (Table 2). A variety of proposed by He, Peng, and Chen.[2c] We instead believe the AQ-masked alkenyl carbonyl compounds (1a–1h) were E-alkene is first isomerized to Z-configuration upon Pd(II) competent substrates in this transformation, providing the coordination, followed by anti-nucleopalladation to give a desired products in moderate to good yields with satisfactory common alkylpalladium intermediate in both cases (vide infra). er. The absolute configurations of products 4f and 4g were Gratifyingly, AQ-masked 4-pentenoic acid substrate 1i assigned as (R, R) by X-ray crystallography analysis, and underwent this transformation smoothly through a putative other products were assigned by analogy.
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