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

Experimental for chapter 3.1
CHOH), 4.04 (d, 1H, J 6.5, CHNH 2 ), 2.44 (br, 2H, NH 2 ); 13 C-NMR (CDCl 3 , 75 MHz)
δ 142.3 (Ph CCOH), 141.6 (Ph CCNH 2 ), 128.6, 127.9, 127.4, 127.4, 127.0, 126.4 (Ph),
78.0 (COH), 62.5 (CNH 2 ).
Synthesis of (2R,3R)-1-benzoyl-2,3-diphenylaziridine (100a)
O
Cl
H
N
Et 3 N, petrol/Et 2 O
O
N
Ph
Ph
Ph
Ph
Adapted from the method of Lygo, 15 benzoyl chloride (0.084 cm 3 , 0.73 mg) was
dissolved in petrol (2 cm 3 ) and added drop wise to a solution of aziridine 173 (150 mg,
0.77 mmol) in petrol (5 cm 3 ), Et 2 O (2 cm 3 ) and Et 3 N (0.01 cm 3 , 0.80 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 (30 cm 3 ), filtration over celite and
evaporation, yielding aroyl aziridine 100a (c. 185 mg, 84%) as a clear oil which was
used without purification.
R f : 0.37 (9:1 petrol:EtOAc); MS m/z (CI+): 300 (100%, MH + ), 301 (13%, (M+1)H + );
IR ν max (film)/cm -1 : 3033 (CH), 1668 (CO), 1602, 1497; 1 H-NMR (CDCl 3 , 300 MHz)
δ 7.96 (d, 2H, J 8.5, ortho-Ph), 7.45-7.30 (m, 13H, Ar), 4.04 (s, 2H, CHPh); 13 C-
NMR (CDCl 3 , 75 MHz) δ 175.7 (CO), 135.5, 133.5, 132.3, 128.7, 128.5, 128.0, 127.9,
126.4 (Ph), 49.0 (CHPh).
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