A Route to Carbasugar Analogues - Jonathan Clayden - The ...

Experimental for chapter 3.1
Synthesis of (2R,3R)-1-(4-methoxybenzoyl)-2,3-diphenylaziridine (100b)
O Cl
OMe
H
N
Ph Ph
Et 3 N, petrol/Et 2 O
+ 1
Ph
O N
Ph
OMe
Adapted from the method of Lygo, 15 p-anisoyl chloride (800mg, 4.71mmol) was
dissolved in petrol (10 cm 3 ) and added drop wise to a solution of aziridine (1.00g, 5.12
mmol) in petrol (25 cm 3 ), Et 2 O (10 cm 3 ) and Et 3 N (0.71 cm 3 , 5.12 mmol) at –10 °C
and stirred until complete (IR). The resulting suspension was allowed to warm to
room temperature before trituration with Et 2 O (200 cm 3 ), filtration over celite and
evaporation, yielding aroyl aziridine 100b (1.38 g, 89%) as colourless clear needles.
2
3
4
R f : 0.29 (4:1 petrol:EtOAc); Mpt: 72 °C (Et 2 O); [α] 23 D +72 (c = 1.4, CH 2 Cl 2 ); MS m/z
(CI+): 330 (100%, MH + ), 331 (22%, (M+1)H + ); HRMS (ESI+) m/z found 330.1493
(MH calcd. 330.1489); IR ν max (film)/cm -1 : 1660 (C=O), 1604, 1510, 1321 (m), 1257
(m); 1 H-NMR (CDCl 3 , 500 MHz) δ 7.86 (d, 2H, J 9.0, H2), 7.90-6.71 (m, 10H, Ph H),
6.74 (d, 2H, J 9.0, H3), 3.93 (s, 2H, CH), 3.75 (s, 3H, OMe); 13 C-NMR (CDCl 3 , 125
MHz) δ 175.0 (C=O), 162.8 (C4), 135.8 (ipso-Ph), 130.8, 128.6, 128.5, 127.9, 127.3,
126.4, 126.2, 125.4 (Ar), 113.3 (C3), 55.2 (OMe), 49.1 (CN).
Synthesis of (2R,3R)-1-(3-methoxybenzoyl)-2,3-diphenylaziridine (100c)
O
Cl
Ph
OMe
Ph
H
N
Ph
i-Pr 2 EtN, petrol/Et 2 O
6
O
5
4
N
Ph
1
2
3
OMe
Adapted from the method of Lygo, 15 m-anisoyl chloride (145 mg, 0.12 cm 3 , 0.85
mmol) was dissolved in pentane (2 cm 3 ) and added drop wise to a solution of aziridine
173 (200 mg, 1.02 mmol) in petrol (5 cm 3 ), Et 2 O (2 cm 3 ) and i-Pr 2 EtN (0.18 cm 3 , 1.02
mmol) at –10 °C and stirred until complete (IR). The resulting suspension was
allowed to warm to room temperature before tritriation with Et 2 O (30 cm 3 ), filtration
216