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7a
Nozaki K.
Itoi Y.
Shibahara F.
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8a Kawashima M, and Kakayama M. inventors; Japan
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9 During preparation of this manuscript,
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Larsen RD.
Reider PJ.
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10 The enantiomeric purity of (S)-12 and (S)-14 were determined
to be both >98% by HPLC analysis using chiral stationary
phase column (Daicel Chiracel OD-H, eluent:
n-hexane-isopropanol = 10:1).
11a
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12 Compounds 17a-c were obtained as single diastereomers.
13 Specific rotation data of 18a-d: 18a: [α]D
25 -97.75
(c 0.75, THF). 18b: [α]D
25 -16.93
(c 0.48, THF). 18c: [α]D
25 -54.95 (c 0.58, THF). 18d: [α]D
25 -7.28
(c 0.49, THF).
14 ArgoGel amino resin (1% DVB
cross-linked) purchased from Argonaut Technologies Inc. was used.
15 Aminomethylated polystyrene (1% DVB
cross-linked) was purchased from Novabiochem.
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17 MeO-PEG5000 amino resin was purchased
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Sieber F.
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19a
Immobilization of Boxax Ligands: A typical
procedure is given for the preparation of the PS-PEG resin-supported ligand 4. Boxax methyl ester 18 and
LiOH·H2O (1.05 equiv to methyl ester) was stirred
in a mixture of THF/H2O at 25 °C
for 24 h. After removal of the solvent in vacuo a white precipitate 19 was obtained. A mixture of 19 (1.1 equiv to an amino residue of resin),
HOBt (1.0 equiv) and EDCI (2.5 equiv) and PS-PEG amino resin in
DMF was shaken at 25 °C for 12 h. To a reaction
mixture was added EDCI (5 equiv) and the mixture was continuously
shaken for an additional 24 h during which the progress of the reaction
was monitored by a Kaiser test.
[19b]
The
reaction mixture was filtered and the resin beads were rinsed with
DMF, MeOH and DCM to give a polymer resin supported boxax ligand.
A negative Kaiser test and 13C-MASNMR
studies indicated the complete consumption of the terminal amino
residue of the starting resin and the exclusive formation of the
desired PS-PEG supported boxax ligands. The loading value of the polymer-supported
boxax ligands 4a-d were
estimated to be 0.35 mmol/g based on the initial loading
value of the amino residue. 13C-MASNMR
data of 4a-d: 4a: δ = 17.92, 18.25, 31.35,
32.36, 37.33, 39.01, 69.64, 72.08, 124.86, 125.39, 131.29, 132.62,
133.79, 134.04, 134.12, 137.33, 137.63, 139.31, 163.31, 171.63. 4b: δ = 31.26, 37.12,
38.94, 74.10, 131.23, 132.58, 133.97, 134.27, 137.46, 137.81, 139.70, 142.05,
164.68, 171.68. 4c: δ = 25.21,
31.34, 33.27, 37.43, 39.00, 67.74, 75.75, 124.66, 125.18, 131.39,
132.69, 133.95, 134.18, 137.74, 137.81, 138.02, 139.28, 162.75,
171.68. 4d: δ = 27.67,
31.30, 37.29, 39.00, 66.53, 78.96, 125.40, 131.17, 132.50, 133.60,
133.88, 136.54, 136.82, 139.35, 163.06, 171.59.
19b
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Colescott RL.
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20
General Procedure
for the Asymmetric Wacker-Type Cyclization of 1: A mixture
of immobilized catalyst (0.02 mmol Pd), 2-(2,3-dimethyl-2-butenyl)-phenol(1) (0.2 mmol, 35.2 mg), benzoquinone (0.8
mmol, 86.4 mg) and MeOH (1 mL) was agitated at 60 °C
with shaking for 20 h. After being cooled to r.t., the resin was
filtered off and washed twice with MeOH (1 mL). The solvent was
removed in vacuo and the residue was purified by column chromatography
using silica gel and n-hexane-EtOAc
(95:5) giving (S)-2-iso-propenyl-2-methyl-2,3-dihydrobenzofuran(2) as colorless oil. The ee was determined
by GC (chiral stationary phase capillary column Cyclodex CB).
For recent examples of PEG-supported
binaphthyl-based chiral catalysts, see:
21a
Guerreiro P.
Ratovelomanana-Vidal V.
Genet J.-P.
Dellis P.
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2001,
42:
3423
21b
Fan Q.-H.
Deng G.-J.
Lin C.-C.
Chan ASC.
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2001,
12:
1241
21c
Yang X.-W.
Sheng J.-H.
Da C S.
Wang H.-S.
Su W.
Wang R.
Chan ASC.
J.
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2000,
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21d
Fan Q.-H.
Deng G.-J.
Chen X.-M.
Xie W.-C.
Jiang D.-Z.
Liu
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Chan ASC.
J. Mol. Cat. A.
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37 ; see also ref. 2b
For recent examples of PEG-supported
chiral oxazoline ligands, see:
22a
Annunziata R.
Benaglia M.
Cinquini M.
Cozzi F.
Pitillo M.
J.
Org. Chem.
2001,
66:
3160
22b
Glos M.
Reiser O.
Org. Lett.
2000,
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