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Synlett

Volumn , Issue 4, 2009, Pages 675-680

Synthesis and evaluation of chiral dibenzazepinium halide phase-transfer catalysts

(5) Lygo, Barry a Allbutt, Bryan a Beaumont, Douglas J a Butt, Umar a Gilks, James A R a

a UNIVERSITY OF NOTTINGHAM (United Kingdom)

Author keywords

Amino acids; Asymmetric alkylation; Michael addition; Phase transfer catalysis; Quaternary ammonium salts

Indexed keywords

EID: 62349095651 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087810 Document Type: Article

Times cited : (21)

References (42)

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21
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- R = 28.2 min (S)-isomer.

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42
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- General Procedure for the Michael Addition of Glycine Imine 11 to MVK A mixture of imine 11 (0.12 mmol) and catalyst (1 mol, in i-Pr2O (4 mL) was cooled to 0 °C. MVK (0.24 mmol) was added followed by anhyd Cs2CO3 (0.06 mmol) and the mixture stirred at 0 °C for 2 h. The mixture was then filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (Rf, 0.2; PE-EtOAc-Et3N, 89:10:1) to give 12 as a colourless oil. IR (CHCl3, νmax, 1739, 1715, 1622 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.67-7.63 (2 H, m, ArH, 7.43-7.26 (16 H, m, ArH, 7.10-7.06 (2 H, m, ArH, 6.89 (1 H, s, CHPh2, 4.19 (1 H, app. t, J, 6.0 Hz, NCH, 2.58-2.50 (1 H, m, 2.44-2.36 (1 H, m, 2.23-2.18 (2 H, m, 2.05 (3 H, s, Me, 13C NMR (100 MHz, CDCl3, δ, 208.0 C, 171
- R = 29.5 min (S)-isomer.

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