Alessandra Lattanzi et al.
FULL PAPERS
over a celite bed with ethyl acetate (40mL), the solvent was
evaporated under vacuum and the crude reaction mixture
was purified by flash chromatography (from petrol/ethyl
acetate mixtures 90/10 to pure ethyl acetate) to give exo-3
(80–90% mol recovery with respect to 4) and 6. Spectro-
scopic data of sulfoxides 6 were in agreement with those re-
ported in the literature.[4] Enantiomeric excesses and abso-
lute configurations were determined by HPLC analysis on
chiral column (Daicel Chiralcel OB and OD columns) with
UV detection at 254 nm according to the literature.[4,20,23]
(R)-4-Tolyl methyl sulfoxide (6a): 1HNMR (400 MHz):
d=7.53 (d, J=8.0Hz, 2H), 7.33 (d, J=8.0Hz, 2H), 2.71 (s,
3H), 2.42 (s, 3H); HPLC: tr (R)=20.5 min, tr (S)=9.7 min
(Chiralcel OB; flow rate 0.8 mLminÀ1; hexane/i-PrOH, 8/2).
(R)-Phenyl methyl sulfoxide (6b): 1HNMR (400 MHz):
d=7.65–7.63 (m, 2H), 7.54–7.52 (m, 3H), 2.72 (s, 3H);
HPLC: tr (R)=20.2 min, tr (S)=12.1 min (Chiralcel OB;
flow rate 0.8 mLminÀ1; hexane/i-PrOH, 8/2).
(R)-4-Methylbenzyl-4’-tolyl sulfoxide (6l): 1HNMR
(400 MHz): d=7.32–7.17 (m, 4H), 7.04 (d, J=7.0Hz, 2H),
6.85 (d, J=7.0Hz, 2H), 4.06 (d, J=12.5 Hz, 1H), 3.93 (d,
J=12.5 Hz, 1H), 2.40(s, 3H), 2.32 (s, 3H); HPLC: tr (R)=
17.0min, tr (S)=18.6 min (Chiralcel OD; flow rate
0.7 mLminÀ1; hexane/i-PrOH, 9/1).
Acknowledgements
This work was co-funded by MIUR within the national
PRIN (2004) framework.
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(R)-2-Naphthyl
methyl
sulfoxide
(6f):
1HNMR
(400 MHz): d=8.22 (s, 1H), 8.00–7.98 (d, J=8.8 Hz, 1H),
7.94–7.92 (m, 2H), 7.61–7.59 (m, 3H), 2.80(s, 3H); HPLC:
tr (R)=20.4 min, tr (S)=14.8 min (Chiralcel OB; flow rate
0.8 mLminÀ1; hexane/i-PrOH, 8/2).
1
(R)-Phenyl ethyl sulfoxide (6g): HNMR (400 MHz): d=
7.62–7.60(m, 2H), 7.53–7.51 (m, 3H), 2.86–7.83 (m, 2H),
1.20(t, J=7.4 Hz, 3H); HPLC: tr (R)=17.8 min, tr (S)=
9.5 min (Chiralcel OB; flow rate 0.8 mLminÀ1; hexane/i-
PrOH, 8/2).
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d=7.50–7.35 (m, 5H), 7.31–7.20 (m, 3H), 7.00–6.95 (m,
2H), 4.08 (d, J=12.6 Hz, 1H), 3.98 (d, J=12.6, 1H);
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1
(R)-Benzyl methyl sulfoxide (6i): HNMR (400 MHz): d=
7.40–7.23 (m, 5H), 4.07 (d, J=12.8 Hz, 1H), 3.93 (d, J=12.8
Hz, 1H), 2.46 (s, 3H); HPLC: tr (R)=16.5 min, tr (S)=
13.0min (Chiralcel OB; flow rate 0.8 mLmin À1; hexane/i-
PrOH, 8/2).
1
(R)-Benzyl 4-tolyl sulfoxide (6j): HNMR (400 MHz): d=
7.34–7.20(m, 7H), 7.02–6.98 (m, 2H), 4.10(d,
J=12.6 Hz,
1H), 3.94 (d, J=12.6 Hz, 1H), 2.40(s, 3H); HPLC: tr (R)=
9.8 min, tr (S)=11.4 min (Chiralcel OD; flow rate
0.8 mLminÀ1; hexane/i-PrOH, 8/2).
(R)-Benzyl 4-bromophenyl sulfoxide (6k): 1HNMR
(400 MHz): d=7.58–7.53 (m, 2H), 7.32–7.25 (m, 3H), 7.22–
7.18 (m, 2H), 7.00–6.95 (m, 2H), 4.09 (d, J=12.6 Hz, 1H),
3.97 (d, J=12.6 Hz, 1H); HPLC: tr (R)=12.9 min, tr (S)=
14.3 min (Chiralcel OD; flow rate 0.8 mLminÀ1; hexane/i-
PrOH, 8/2).
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