Reference and Notes
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<A NAME="RD31208ST-17">17</A>
(
S
)-2-Dibenzylamino-6-(dimethoxyphosphoryl)-5-oxohexanoic
Acid Benzyl Ester (5)
To a soln of dimethyl methylphosphonate
(0.191 g, 1.54 mmol) in dry THF (17 mL) cooled at -78 ˚C,
BuLi (0.62 mL of a 2.5 M soln in hexane) was added dropwise. After
40 min, a soln of 4 (0.390 g, 7.7 mmol)
in dry THF (14 mL) was added. After stirring for 4 h at -78 ˚C,
a sat. soln of NH4Cl (6 mL) was added followed by EtOAc
(30 mL). After warming to r.t., the organic phase was separated.
The aqueous phase was extracted with EtOAc, all the organic fractions
were collected and dried over Na2SO4. The
solvent was removed in vacuo, and the crude material was purified by
column chromatography (PE-EtOAc, 1:3) to give compound 5 as colourless oil (0.26 g, 65% yield). ¹H
NMR (400 MHz, CDCl3): δ = 1.95-2.02
(m, 2 H, H-3), 2.41-2.78 (m, 2 H, H-4), 2.79-2.97
(m, 2 H, H-6), 3.29 (t, J = 6.8
Hz, 1 H, H-2), 3.67 (AB system, 4 H, NCH2Ph), 3.68 (d, J = 2.8 Hz,
3 H, OCH3), 3.71 (d, J = 2.8
Hz, 3 H, OCH3), 5.19 (AB system, 2 H, OCH2Ph),
7.19-7.36 (m, 15 H, ArH). ¹³C
NMR (50 MHz, CDCl3): δ = 22.6,
40.0, 40.4, 42.5, 52.8, 53.0, 54.4, 59.8, 66.1, 127.1 54.5, 59.8,
66.2, 127,1, 128.2, 128.3, 128.5, 128.6, 128.9, 135.9 (2 C), 139.21,
172.13, 200.7, 200.8. HRMS (ES): m/z calcd
for C29H35NO6P [M + H]+: 524.2202;
found: 524.2180.
<A NAME="RD31208ST-18">18</A>
Petricci E.
Mann A.
Rota A.
Schoenfelder A.
Taddei M.
Org. Lett.
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For the domino hydroformylation-Wittig
reaction, see:
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Breit B.
Zhan SK.
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Zhan SK.
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2005,
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<A NAME="RD31208ST-20">20</A>
(
S
,
E
) 2-Dibenzylamino-5-oxoicos-6-enoic
Acid Benzyl Ester (11) - General Procedure
To
a soln of 5 (0.900 g, 1.7 mmol) in dry
MeCN (18 mL), dry LiCl (72.0 mg, 1.7 mmol) was added followed by DIPEA
(180 mg, 239 µL, 1.4 mmol). After stirring for 2 h at r.t.,
tetradecanal (0.276 g, 1.3 mmol) in MeCN was added and the mixture
stirred at r.t. for 72 h. Brine was added
and the organic
layer separated. The aqueous phase was extracted with EtOAc, all
the organic fractions were collected and dried over Na2SO4.
The solvent was removed under vacuum and the crude mixture was purified
by column chromatography (PE-EtOAc, 5:1) to give compound 11 as a colourless oil (0.673 g, 85% yield); [α]D
²5 -55.5
(c 0.1, CHCl3). ¹H
NMR (400 MHz, CDCl3): δ = 0.91 (t, J = 6.6 Hz, 3
H), 1.24-1.47 (m, 20 H), 1.45 (m, 2 H), 2.07-2.19
(m, 4 H), 2.41-2.69 (m, 2 H), 3.39 (dd, J = 8.4,
6.2 Hz, 1 H), 3.73 (AB system, 4 H), 5.23 (AB system, 2 H), 6.00
(d, J = 15.6 Hz,
1 H), 6.71 (dt, J = 15.6,
7.0 Hz, 1 H), 7.22-7.43 (m, 15 H). ¹³C
NMR (100 MHz, CDCl3): δ = 14.0, 20.8,
22.6, 23.3, 28.0, 29.1, 29.2, 29.3 (3 C), 29.4, 29.5, 31.8 (2 C),
32.3, 36.3, 54.4, 60.1, 65.9, 126.9 (3 C), 128.1 (4 C), 128.2 (2
C), 128.4 (4 C), 128.7 (2 C), 130.1, 135.9, 139.2 (2 C), 147.2,
172.2, 199.3. MS (ES): m/z = 632 [M + Na]+.
(2
S
,5
R
)-5-Pentadecylpyrrolidine-1,2-dicarboxylic Acid 1-
tert
-Butyl Ester
(21) - General Procedure
To a soln of 11 (100 mg, 0.16 mmol) in CH2Cl2-MeOH
(1:9, 5 mL) placed in the bottle connected with a Parr apparatus, Boc2O
(54 mg, 0.25 mmol) and Pd(OH)2/C (20%,
9 mg, 0.012 mmol) were added. The bottle was filled with H2 at
4.8 bar and shaken at r.t. for 8 h. The bottle was degassed, the catalyst
filtered (attention: the residue Pd may
be pyrophoric) and washed several times with MeOH. The solvent was
removed under vacuum and the crude mixture was purified by column
chromatography (CHCl3-MeOH, 98:2) to give compound 21 as white gel (51 mg, 75% yield); [α]D
²5 -20.7
(c 0.1, CDCl3). ¹H
NMR (400 MHz, CHCl3):
δ = 0.84
(t, J = 7.2
Hz, 3 H), 1.09-1.43 (m, 26 H), 1.47 (s, 9 H), 1.59-1.67
(m, 2 H), 1.82-1.94 (m, 2 H), 1.95-2.28 (m, 2 H),
3.71-3.83 (m, 1 H), 4.18-4.26 (m, 1 H), 9.91 (br
s, 1 H). ¹³C NMR (100 MHz, CDCl3): δ = 14.0,
22.7, 26.6, 28.3 (3 C), 29.3 (2 C), 29.7 (10 C), 31.9, 34.3, 58.9,
60.0, 67.0, 173.7, 179.4. MS (ES): m/z = 424 [M - H]-.
<A NAME="RD31208ST-21">21</A>
Piras L.
Genesio E.
Ghiron C.
Taddei M.
Synlett
2008,
1125
<A NAME="RD31208ST-22">22</A>
Crystallographic data (excluding structure
factors) for X-ray crystal structure of 18 have
been deposited with the Cambridge Crystallographic Data Centre as
supplementary publication no. CCDC 710555. Copies of the data can
be obtained, free of charge, on application to CCDC, 12 Union Road,
Cambridge, CB2 1EZ, UK [fax: +44 (1223)336033
or e-mail: deposit@ccdc.cam.ac.uk].
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J. Org. Chem.
2007,
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