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Synlett 2012; 23(12): 1797-1800
DOI: 10.1055/s-0031-1290405
DOI: 10.1055/s-0031-1290405
letter
Lewis Base Organocatalyzed Enantioselective Hydrosilylation of 1,4-Benzoxazines
Further Information
Publication History
Received: 02 April 2012
Accepted after revision: 06 May 2012
Publication Date:
21 June 2012 (online)
Abstract
A chiral Lewis base organocatalyzed enantioselective hydrosilylation of 1,4-benzoxazines is presented. The reactions afforded various enantioenriched 3-substituted dihydro-2H-1,4-benzoxazines with high yields (up to 98%) in moderate enantioselectivities (up to 87% ee).
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
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- 9 Enantioselective Hydrosilylation of Benzoxazine; General Procedure: Trichlorosilane (51 μL, 0.5 mmol, 2.0 equiv) dissolved in THF (0.15 mL) was added to a stirred solution of 1,4-benzoxazine 2 (0.25 mmol) and catalyst (0.025 mmol) in anhydrous THF (2 mL) at 0 °C. The mixture was stirred at the same temperature for 12 h, then quenched with sat. aq NaHCO3 and extracted with EtOAc. The combined extract was washed with brine and dried over anhydrous Na2SO4 and the solvents were evaporated. Purification by column chromatography (silica gel; hexane–EtOAc) afforded pure product 3. The ee values were determined by using established HPLC techniques with chiral stationary phases
- 10 3-(Furan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (3l): Yield: 90%; light-yellow oil; 87% ee. 1H NMR (300 MHz, CDCl3): δ = 7.39 (d, J = 0.9 Hz, 1 H), 6.84–6.78 (m, 2 H), 6.72–6.65 (m, 2 H), 6.36 (dd, J = 1.8, 3.2 Hz, 1 H), 6.30 (d, J = 3.2 Hz, 1 H), 4.63–4.62 (m, 1 H), 4.43–4.38 (m, 1 H), 4.23 (dd, J = 7.0, 10.6 Hz, 1 H), 4.10 (br s, 1 H). 13C NMR (75 MHz, CDCl3): δ = 152.5, 143.4, 142.2, 132.6, 121.5, 119.2, 116.6, 115.6, 110.4, 106.7, 67.8, 48.3. HPLC (OD-H column; n-hexane–2-propanol, 80:20; flow rate = 1.0 mL/min): t R = 8.08 (minor), 9.12 (major) min; [α]D 20 +32.6 (c = 0.4, CHCl3). HRMS (ESI): m/z [M + H]+ calcd. for C12H11NO2 + H+: 202.0863; found: 202.0865
For selected examples, see:
For reviews on Lewis base activation of Lewis acids, see:
For reviews, see:
For representative examples, see: