References
1 Current address: Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield S3 7HF, UK.
2a
Myers AG.
Yang BH.
Chen H.
Gleason JL.
J. Am. Chem. Soc.
1994,
116:
9361
2b
Micouin L.
Schanen V.
Riche C.
Chiaroni A.
Quirion J.-C.
Husson H.-P.
Tetrahedron Lett.
1994,
35:
7223
2c
Myers AG.
Gleason JL.
Yoon T.
J. Am. Chem. Soc.
1995,
117:
8488
2d
Myers AG.
Yoon T.
Tetrahedron Lett.
1995,
36:
9429
2e
Micouin L.
Jullian V.
Quirion J.-C.
Husson H.-P.
Tetrahedron: Asymmetry
1996,
7:
2839
3 Bull S. D., Davies S. G., Jones S., Sanganee H. J.; J. Chem. Soc., Perkin Trans. 1; 1999, 387
4 Analytical samples were prepared by column chromatography and/or recrystallisation. All new compounds reported had satisfactory analytical data that will be reported in full in due course.
5
Typical Experimental Procedure: n-BuLi (1.6 M, 0.44 mL, 0.70 mmol) was added to a solution of N-methyl 4(S)-iso-propyl oxazolidin-2-one (0.1 g, 0.70 mmol) at -78 °C. The reaction was warmed to 0 °C and after 2 h quenched with H2O (2 mL) and extracted with EtOAc (5 × 10 mL). The organic extracts were combined and washed with NH4Cl (5 mL), dried over NaSO4 and the solvent removed under vacuum to give a pale yellow oil as the crude product
(0.157 g) which was purified using flash column chromatography (EtOAc) to give a clear oil (0.131 g, 93%); [α]D
25 -23.1 (c 2.5, CHCl3); ratio of rotamers A/B = 1.7:1. Rotamer A: 1H NMR (500 MHz, CDCl3): δ = 0.80 (d, J = 6.4 Hz, 3 H, CH
3
CH), 0.86 (t, J = 7.3 Hz, 3 H, CH
3
CH2), 0.93 (d, J = 6.4 Hz, 3 H, CH
3
CH), 1.29 (m, 2 H, CH3CH
2
), 1.55 (m, 2 H, CH3CH2CH
2
), 1.84 [m, 1 H, (CH3)2CH], 2.33 (m, 2 H, CH3CH2CH2CH
2
), 2.84 (s, 3 H, NCH
3
), 3.24 (s, br d, 1 H, OH), 3.97-3.42 (range of multiplets, 3 H, HOCH
2
CH). 13C NMR (125 MHz, CDCl3): δ = 22.7 (CH3CH), 27.6 [(CH3)CH2
CH2], 27.7 [(CH3)2
CH], 34.1 [CH3(CH2)2
CH2], 61.9 (HOCH2), 65.6 (HOCH2
CH), 175.4 [C(O)N]. Rotamer B: 1H NMR (500 MHz, CDCl3): δ = 0.77 (d, J = 6.7 Hz, 3 H, CH
3
CH), 0.85(t, J = 7.3 Hz, 3 H, CH
3
CH2), 0.91(d, J = 6.4 Hz, 3 H, CH
3
CH), 1.68 [m, 1 H, (CH3)2CH], 2.28 (m, 2 H, CH3CH2CH2CH
2
), 2.68 (s, 3 H, NCH
3
), 3.24 (s, br d, 1 H, OH), 3.97-3.42 (range of multiplets, 3 H, HOCH
2
CH). 13C NMR (125 MHz, CDCl3): δ = 14.0 (CH3CH), 26.8 [(CH3)2
CH], 27.3 (CH3CH2
CH2), 32.1 (N-CH3), 33.4 [CH3(CH2)2
CH2], 60.8 (HOCH2), 63.3 (HOCH2
CH), 175.1 [C(O)N]. MS (EI): m/z calcd [M+] for C11H23NO2: 201.1729; found: 201.1719. MS (EI): m/z (%) = 201 (1) [C11H23NO2
+], 183 (2), 170 (1) [C10H20N+], 86 (100), 74 (44).
6
Jullian V.
Quirion J.-C.
Husson H.-P.
Synthesis
1997,
1091
7
Jarowicki K.
Kocienski PJ.
Qun L.
Org. Synth.
2002,
79:
11
8
Phillips AJ.
Uto Y.
Wipf P.
Reno MJ.
Williams DR.
Org. Lett.
2000,
2:
1165