Preparation of Monomethyl Fumarate

Asymmetric syn-dihydroxylation of γ-substituted (2R)-N-(β,γ-enoyl)bornane-10,2-sultams

“…MS: 375 (8, M"), 162 (20), 161 (loo), 133 (13), 118 (5), 77 (5), 43 (5). 6R, 7~iR)-1,4,5.6.7.7u-He.ucrhydro-8,8- 1315,1115,837.1H-NMR:8.22(m,2H);7.78(d,J=16,1H);7.66(m,2H);7.28(d,J=16,1H);4.0(f,J=7, 1 H); 3.59(d, J = 14, 1 H); 3.49(d, J = 14,l H); 2.17(m, 2 H); 1.93 (m, 3 H); 1.3-1.6(m, 2 H); 1.20(s, 3 H); 1.00 65.3 (C(2)); 53.1 (C(10)); 48.7 (C(1)); 47.9 (C(7)); 44.6 (C(4)); 38.4 (C(3)); 32.8 (C(6)); 26.5 (C(5)); 20.8 (C(8)); 19.9 (C(9)). MS: 390 (4, M"), 326 (6), 283 and 4-methylmorpholine 4-oxide (2.0 mmol) were dissolved in r-BuOH/DMF 1 : 1 (10 ml).…”

“…[(3uS,6R. 7aR) -1,4,5,6,7,7a-hexahpdro-8.8-dimeth~~l-3H-3a,6-metlrano[2 07(dd,J=7.8,13.8,2H);1.96-1.85(m,6H);1.45-1.39(m,2H);1.36-1.29(m,2H);1.17(s,6H); 38.0 (C(3)); 32.8 (C(6)); 26.3 (C(5)); 20.9 (C(8)); 19.8 (C (9) N-[(2'R,3'S)-2',3'-Dihydro.~y-3'-phen~~lpropanoylJhornane-10.2-sultam ( = (3aS,6R,7aR)-l-[(2R,3Si-2,3-Dihydroxy-l-o.uo-3-phenylpropyl]-1.4.5.6.7.7a-hexahydro-8.8-dimethyl-3H-3a.6-me~hano~2,l] 6 H). I3C-NMR: 169.6 (C(1')); 70.6 (C(2')); 65.2 (C(2)); 52.8 (C(10)); 49.1 (C(1)); 47.8 (C(7)); 44.7 (C(4));…”

“…152 (40) d,J=4,1OH):3.46(d,J=14,1H);2.97(d,J=4,lOH);2.22(m,l H);2.08(dd.J=8,13.1 H);1.9(ni,3H); 1.3-1.47 (m, 2 H); 1.16 (s, 3 H); 0.98 (s, 3 H). I3C-NMR: 171.0 (C(1')); 159.3 (C,,); 131.4 (C,pJ: 128.0 (2C"); 113.8 ( 2 CJ: 73.7 (C(3')); 71.9 (C(2')); 65.2 (C(2)); 55.2 (MeO): 52.8 (C(10)); 49.2 (C(1)); 47.9 (C(7)); 44.5 (C(4)); 38. 0 (C(3)); 32. 8 (C(6)); 26.4 (C(5)); 20.8 ((78)); 19.8 (C(9)). MS. 409 (0.…”

“…The previously unreported (2R)-N-[(E)-3-(methoxycarbonyl)prop-2-enoyl]bornane-10,2-sultam (( -)-lb)3) was conveniently obtained in 65 YO yield by acylation of (2R)-bornane-10,2-sultam on successive treatment with NaH (1 .O mol-equiv.) and monomethyl ester of fumaroyl chloride (= methyl (E)-4-chloro-4-oxobut-2-enoate) [19]. Oxidation of ( -)-lb (0.3 mol-equiv.…”

“…4-[(3aS, 6R,7aR)-l,4,5.6.7.7a-Hesaliydro-8,8-dimetl1~l-3~-3u,6-me~h~1no[2,l] 3 H). I3C-NMR: 165,0(MeOOC); 162.4(C(I')); 133,6(C(2')); 132.3 (C(3')); 65.1 (C(2)); 53.0 (MeO); 52.3 (C(10)); 48.7 (C(1)); 47.8 (C(7)); 44.6 (C(4)); 38.2 (C(3)); 32.8 (C(6)); 26.4 (C(5)); 20.8 (C(8)); 19.8 (C (9) 6R,7aR) -1.4,5.6,7,7a-hexah? ;dro-8,~-dimeth,vl-3~-3u,6-methuno[2, l]henzi.ro~hiazolej 2.2.2',2'-Tetruo-ride; (-)-lc).…”