Asymmetric α-Amination Reaction of Alkenoate Cyclic Esters Catalyzed by Chiral Tin Alkoxides

Akira Yanagisawa; Yoshiki Yamashita; Chika Uchiyama; Ryuta Nakano; Moe Horiguchi; Kazuki Ida

doi:10.1055/s-0037-1612278

Synlett, Table of Contents

Synlett 2019; 30(06): 738-742
DOI: 10.1055/s-0037-1612278

letter

Asymmetric α-Amination Reaction of Alkenoate Cyclic Esters Catalyzed by Chiral Tin Alkoxides

Akira Yanagisawa*

Soft Molecular Activation Research Center, Molecular Chirality Research Center, Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan Email: ayanagi@faculty.chiba-u.jp

,

Yoshiki Yamashita

,

Chika Uchiyama

,

Ryuta Nakano

,

Moe Horiguchi

,

Kazuki Ida

› Author Affiliations

Abstract

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Abstract

A catalytic enantioselective α-amination reaction of alkenoate cyclic esters with dialkyl azodicarboxylates was achieved by using a 3,3′-di(1-naphthyl)-substituted (R)-BINOL–dibromostannane complex as a chiral precatalyst in the presence of a sodium alkoxide and an alcohol. Optically active α-hydrazino ketones were obtained in moderate to high yields and with up to 91% ee in the presence of the chiral tin alkoxide generated in situ.

Key words

alkenoate cyclic esters - lactones - amination - asymmetric catalysis - dialkyl azodicarboxylates - tin catalysis

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References

References and Notes

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8 Diethyl 1-(1-Benzoyl-4-ethoxy-1-methyl-4-oxobutyl)hydrazine-1,2-dicarboxylate (4ba); Typical Procedure Chiral tin dibromide 3d ⁷ (10.1 mg, 0.013 mmol) was dissolved in dry MeCN (1.25 mL) at r.t., and the mixture was stirred for 10 min. A solution of NaOEt in EtOH (10.5 μL, 0.025 mmol) and EtOH (175 μL, 3.0 mmol) were added, and the resulting mixture was stirred for 30 min. DEAD (43.5 mg, 0.25 mmol) and lactone 1b (70.5 mg, 0.375 mmol) in dry CHCl₃ (0.25 mL) were added at r.t., and the mixture was stirred for 6 h at r.t. The mixture was then treated with solid KF (0.5 g) and brine (2 mL) at r.t. for 10 min. The resulting precipitate was collected by filtration, and the filtrate was extracted with Et₂O (×3). The combined organic extracts were washed with brine, dried (Na₂SO₄), filtered, and concentrated in vacuo. The residual crude product was purified by column chromatography (silica gel) to give a orange oil; yield: 63.1 mg (62%; 89% ee); [α]_D ^23.8 –111.1° (c 0.47, CHCl₃). The enantioselectivity toward the product was determined by HPLC [Daicel Chiralpak AD-3, hexane–EtOH (20:1), flow rate: 1.0 mL/min]: t ₁ = 42.1 min (major), t ₂ = 64.1 min (minor). TLC: R_f = 0.20 (EtOAc–hexane, 1:3). IR (neat): 3309, 2986, 1714, 1685, 1597, 1447, 1376, 1227, 1187, 1050, 970 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 1.22 (t, J = 7.2 Hz, 6 H, 2 CH₃), 1.35 (t, J = 7.2 Hz, 3 H, CH₃), 1.60 (s, 3 H, CH₃), 2.14–2.22 (m, 1 H, one proton of CH₂), 2.27–2.33 (m, 1 H, one proton of CH₂), 2.50 (m, 1 H, one proton of CH₂), 2.70–2.87 (m, 1 H, one proton of CH₂), 3.66–4.14 (m, 5 H, 2 CH₂ and NH), 4.25–4.32 (m, 2 H, CH₂), 7.37–7.46 (m, 3 H, Ar-H), 8.58 (d, J = 6.8 Hz, 2 H, Ar-H). ¹³C NMR (125.65 MHz, CDCl₃): δ = 14.0 (2 C), 14.4, 24.4, 29.3, 30.6, 60.6, 62.0, 62.7, 70.2, 128.0, 128.2, 128.3, 128.8, 132.0, 135.6, 156.6, 157.2, 175.9, 194.6. HRMS (ESI+): m/z [M + H]⁺ calcd for C₂₀H₂₉N₂O₇: 409.1969; found: 409.1967.

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