References and Notes
For recent reviews, see:
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Trost BM.
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Synthesis
2006,
369
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Quaternary
Stereocenters
Christoffers J.
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Wiley;
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For related palladium-catalyzed
reactions, see:
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Nishimura T.
Matsumura S.
Maeda Y.
Uemura S.
Chem. Commun.
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<A NAME="RY00210ST-10">10</A>
Typical Procedure
for the Preparation of (
S
)-3-[(
tert
-Butyldimethylsilyloxy)methyl]-6-chloro-3-methylindan-1-one
(6c)
tert-Cyclobutanol trans-
1c (40.9
mg, 0.100 mmol), [Rh(cod)(OH)]2 (1.14
mg, 2.50 µmol), (R)-Difluorphos
(L3, 4.10 mg, 6.00 µmol), and
Cs2CO3 (0.150 mmol, 48.9 mg) were weighted
into an oven-dried vial equipped with a magnetic stir bar, capped
with a septum, and purged with nitrogen. Dry xylenes (0.5 mL) were
added, and the mixture was degassed with three freeze-pump-thaw
cycles. The mixture was stirred for 10 min at 23 ˚C
and subsequently immersed into a preheated oil bath (120 ˚C)
for 12 h. After TLC analysis showed the complete conversion, the
reaction mixture was cooled to 23 ˚C and directly purified
on silica gel (pentane-EtOAc 30:1, R
f
= 0.18) giving 32.2
mg (99%, 93% ee) of indanone (S)-
6c as colorless
oil. ¹H NMR (400 MHz, CDCl3): δ = 7.71-7.60
(m, 1 H), 7.54 (dd, J = 8.2,
2.1 Hz, 1 H), 7.45 (dd, J = 8.2,
0.5 Hz, 1 H), 3.62-3.56 (m, 2 H), 2.75 (d, J = 18.7 Hz,
1 H), 2.41 (d, J = 18.7
Hz, 1 H), 1.40 (s, 3 H), 0.77 (s, 9 H), -0.06 (s, 3 H), -0.13
(s, 3 H) ppm.
¹³C NMR (100
MHz, CDCl3): δ = 204.0,
158.2, 138.5, 134.3, 134.1, 125.7, 122.9, 70.7, 48.5, 44.1, 25.6,
23.4, 18.1, -5.7, -5.8. HRMS (EI+): m/z calcd for C13H16ClO2Si [M - C4H9]+:
267.0603; found: 267.0603. IR (ATR): 2955, 2929, 2885, 2856, 1720,
1602, 1470, 1254, 1236, 1180, 1109, 837, 777 cm-¹. [α]D
²0 -21
(c 0.94, CHCl3).
<A NAME="RY00210ST-11">11</A>
The absolute configuration of compounds 6 were assigned in analogy to the reported
cleavage site. See ref. 4c,d, and 6.
