1027
Synlett
N. Shimada et al.
Letter
References and Notes
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(
25) Procedure for the Catalytic Synthesis of Weinreb Amide 4a
(Table 1, Entry 8, 1 g Scale)
11, 4474. (d) Kumar, A.; Akula, H. K.; Lakshman, M. K. Eur. J. Org.
N,O-Dimethylhydroxylamine (3, 25.0 mL, 0.60 M in DCE, 15.0
mmol, 3.0 equiv) was added dropwise over 1 h to a suspension
of diboronic acid anhydride 1 (54.0 mg, 0.100 mmol, 2.0 mol%)
and Boc-Ser-OH (2a, 1.03 g, 5.00 mmol, 1.0 equiv) in DCE (8.3
mL, total 0.15 M) under reflux (bath temp, 90 °C). After stirring
for 24 h under reflux, the reaction mixture was cooled to room
temperature. Concentration under reduced pressure furnished
the crude product, which was purified by silica gel column
Chem. 2010, 2709. (e) Tyrrell, E.; Brawn, P.; Carew, M.;
Greenwood, I. Tetrahedron Lett. 2011, 52, 369. (f) Niu, T.; Wang,
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3
20.
9) Wilson, Z. E.; Fenner, S.; Ley, S. V. Angew. Chem. Int. Ed. 2015, 54,
284.
(
1
(
10) Haridas, V.; Bijesh, M. B.; Chandra, A.; Sharma, S.; Shandilya, A.
Chem. Commun. 2014, 50, 13797.
chromatography (5% MeOH in CHCl ) to give tert-butyl (S)-(3-
3
(
11) Ojima, D.; Yasui, A.; Tohyama, K.; Tokuzumi, K.; Torihara, E.; Ito,
K.; Iwasaki, A.; Tomura, T.; Ojika, M.; Suenaga, K. J. Org. Chem.
hydroxy-1-[methoxy(methyl)amino]-1-oxopropan-2-yl)carba-
mate (4a, 1.02 g, 4.08 mmol, 82%). The optical purity of 4a was
determined to be >99% ee by chiral HPLC analysis.
2
016, 81, 9886.
(
(
(
12) Uma, K.; Lalithamba, H. S.; Raghavendra, M.; Chandramohan,
V.; Anupama, C. ARKIVOC 2016, (iv), 339.
13) Sharnabai, K. M.; Nagendra, G.; Vishwanatha, T. M.; Sureshbabu,
V. V. Tetrahedron Lett. 2013, 54, 478.
Analytical Data for Compound 4a
25
R = 0.35 (CHCl /MeOH = 19:1); []
14.2 (c 1.0, MeOH); mp
f
3
D
1
1
16–117 °C. H NMR (400 MHz, CDCl ): = 5.58 (br s, 1 H), 4.80
3
(
br s, 1 H), 3.83–3.81 (m, 2 H), 3.78 (s, 3 H), 3.23 (s, 3 H), 1.45 (s,
14) (a) Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org. Chem. 1996, 61,
13
9
6
1
H). C NMR (100 MHz, CDCl ): = 171.0, 155.7, 79.8, 63.2,
3
4
196. (b) Ishihara, K.; Ohara, S.; Yamamoto, H. Org. Synth. 2002,
1.5, 52.4, 32.0, 28.2. IR (KBr): = 3473, 3357, 2978, 1060, 1704,
79, 176.
–1
537, 1363, 1297, 1181, 980, cm . HRMS (ESI): m/z calcd for
+
C10H20N NaO5 [M + Na] : 271.1270; found: 292.1266. HPLC
2
?
(CHIRALPAK IC , hexane/i-PrOH = 80:20, 230 nm, flow rate 1.0
mL/min): t = 14.4 min (minor), 26.4 min (major).
R
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2021. Thieme. All rights reserved. Synlett 2021, 32, 1024–1028